MiMeDB: Showing metabocard for O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate (MMDBc0031625)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:53 UTC

Update Date

2022-08-31 18:22:37 UTC

Metabolite ID

MMDBc0031625

Metabolite Identification

Common Name

O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate

Description

O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate is an intermediate in peptidoglycan synthesis. Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is very uniform among all bacteria, and is made up of alternating Œ≤-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-Œ±-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in E. coli most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in E. coli). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08141218162D          

101102  0  0  0  0            999 V2000
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M  CHG  2  74  -1  79  -1
M  END


  Mrv0541 08141218162D          

101102  0  0  0  0            999 V2000
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100 44  1  0  0  0  0
101 46  1  0  0  0  0
M  CHG  2  74  -1  79  -1
M  END
> <DATABASE_ID>
MMDBc0031625

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP(O)(=O)OC1OC(CO)C(O)C(OC2OC(C)C(O)C(O)C2OC(C)=O)C1N=C(C)[O-])=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C71H117NO17P2/c1-49(2)26-16-27-50(3)28-17-29-51(4)30-18-31-52(5)32-19-33-53(6)34-20-35-54(7)36-21-37-55(8)38-22-39-56(9)40-23-41-57(10)42-24-43-58(11)44-25-45-59(12)46-47-83-90(79,80)89-91(81,82)88-70-64(72-61(14)74)68(66(77)63(48-73)86-70)87-71-69(85-62(15)75)67(78)65(76)60(13)84-71/h26,28,30,32,34,36,38,40,42,44,46,60,63-71,73,76-78H,16-25,27,29,31,33,35,37,39,41,43,45,47-48H2,1-15H3,(H,72,74)(H,79,80)(H,81,82)/p-2/b50-28+,51-30+,52-32+,53-34+,54-36+,55-38+,56-40+,57-42+,58-44+,59-46+

> <INCHI_KEY>
WYHMIVUCEAXZMZ-LRILUZMESA-L

> <FORMULA>
C71H115NO17P2

> <MOLECULAR_WEIGHT>
1316.6168

> <EXACT_MASS>
1315.764024283

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
150.46499491884646

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphonato]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
14.540375572700878

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1573268911089687

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8738533442502927

> <JCHEM_PKA_STRONGEST_BASIC>
1.1775807934853026

> <JCHEM_POLAR_SURFACE_AREA>
275.45

> <JCHEM_REFRACTIVITY>
380.3684

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphonato]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   72  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   73  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   75  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   80  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   90  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   91  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   92  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   95  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   96  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   49                                                            
CONECT    2   49                                                            
CONECT    3   50                                                            
CONECT    4   51                                                            
CONECT    5   52                                                            
CONECT    6   53                                                            
CONECT    7   54                                                            
CONECT    8   55                                                            
CONECT    9   56                                                            
CONECT   10   57                                                            
CONECT   11   58                                                            
CONECT   12   59                                                            
CONECT   13   60                                                            
CONECT   14   61                                                            
CONECT   15   62                                                            
CONECT   16   26   27                                                       
CONECT   17   28   29                                                       
CONECT   18   30   31                                                       
CONECT   19   32   33                                                       
CONECT   20   34   35                                                       
CONECT   21   36   37                                                       
CONECT   22   38   39                                                       
CONECT   23   40   41                                                       
CONECT   24   42   43                                                       
CONECT   25   44   45                                                       
CONECT   26   16   49                                                       
CONECT   27   16   50                                                       
CONECT   28   17   50   92                                                  
CONECT   29   17   51                                                       
CONECT   30   18   51   93                                                  
CONECT   31   18   52                                                       
CONECT   32   19   52   94                                                  
CONECT   33   19   53                                                       
CONECT   34   20   53   95                                                  
CONECT   35   20   54                                                       
CONECT   36   21   54   96                                                  
CONECT   37   21   55                                                       
CONECT   38   22   55   97                                                  
CONECT   39   22   56                                                       
CONECT   40   23   56   98                                                  
CONECT   41   23   57                                                       
CONECT   42   24   57   99                                                  
CONECT   43   24   58                                                       
CONECT   44   25   58  100                                                  
CONECT   45   25   59                                                       
CONECT   46   47   59  101                                                  
CONECT   47   46   83                                                       
CONECT   48   63   73                                                       
CONECT   49    1    2   26                                                  
CONECT   50    3   27   28                                                  
CONECT   51    4   29   30                                                  
CONECT   52    5   31   32                                                  
CONECT   53    6   33   34                                                  
CONECT   54    7   35   36                                                  
CONECT   55    8   37   38                                                  
CONECT   56    9   39   40                                                  
CONECT   57   10   41   42                                                  
CONECT   58   11   43   44                                                  
CONECT   59   12   45   46                                                  
CONECT   60   13   65   84                                                  
CONECT   61   14   72   74                                                  
CONECT   62   15   75   85                                                  
CONECT   63   48   66   86                                                  
CONECT   64   68   70   72                                                  
CONECT   65   60   67   76                                                  
CONECT   66   63   68   77                                                  
CONECT   67   65   69   78                                                  
CONECT   68   64   66   87                                                  
CONECT   69   67   71   85                                                  
CONECT   70   64   86   88                                                  
CONECT   71   69   84   87                                                  
CONECT   72   61   64                                                       
CONECT   73   48                                                            
CONECT   74   61                                                            
CONECT   75   62                                                            
CONECT   76   65                                                            
CONECT   77   66                                                            
CONECT   78   67                                                            
CONECT   79   90                                                            
CONECT   80   90                                                            
CONECT   81   91                                                            
CONECT   82   91                                                            
CONECT   83   47   90                                                       
CONECT   84   60   71                                                       
CONECT   85   62   69                                                       
CONECT   86   63   70                                                       
CONECT   87   68   71                                                       
CONECT   88   70   91                                                       
CONECT   89   90   91                                                       
CONECT   90   79   80   83   89                                             
CONECT   91   81   82   88   89                                             
CONECT   92   28                                                            
CONECT   93   30                                                            
CONECT   94   32                                                            
CONECT   95   34                                                            
CONECT   96   36                                                            
CONECT   97   38                                                            
CONECT   98   40                                                            
CONECT   99   42                                                            
CONECT  100   44                                                            
CONECT  101   46                                                            
MASTER        0    0    0    0    0    0    0    0  101    0  204    0
END

Synonyms

Value	Source
O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphoric acid	Generator
N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphonato]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidic acid	Generator

Molecular Formula

C₇₁H₁₁₅NO₁₇P₂

Average Mass

1316.6168

Monoisotopic Mass

1315.764024283

IUPAC Name

N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphonato]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate

Traditional Name

N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphonato]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP([O-])(=O)OP(O)(=O)OC1OC(CO)C(O)C(OC2OC(C)C(O)C(O)C2OC(C)=O)C1N=C(C)[O-])=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C71H117NO17P2/c1-49(2)26-16-27-50(3)28-17-29-51(4)30-18-31-52(5)32-19-33-53(6)34-20-35-54(7)36-21-37-55(8)38-22-39-56(9)40-23-41-57(10)42-24-43-58(11)44-25-45-59(12)46-47-83-90(79,80)89-91(81,82)88-70-64(72-61(14)74)68(66(77)63(48-73)86-70)87-71-69(85-62(15)75)67(78)65(76)60(13)84-71/h26,28,30,32,34,36,38,40,42,44,46,60,63-71,73,76-78H,16-25,27,29,31,33,35,37,39,41,43,45,47-48H2,1-15H3,(H,72,74)(H,79,80)(H,81,82)/p-2/b50-28+,51-30+,52-32+,53-34+,54-36+,55-38+,56-40+,57-42+,58-44+,59-46+

InChI Key

WYHMIVUCEAXZMZ-LRILUZMESA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenyl phospho carbohydrates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol diphosphate
Polyprenyl phospho carbohydrate
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
N-acyl-alpha-hexosamine
Disaccharide phosphate
O-glycosyl compound
Glycosyl compound
Disaccharide
Organic pyrophosphate
Isoprenoid phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	0.0005 g/L	ALOGPS
logP	7.71	ALOGPS
logP	14.54	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	1.18	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	275.45 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	380.37 m³·mol⁻¹	ChemAxon
Polarizability	150.46 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	splash10-014i-2009000000-62f824512033aaf00aa4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-2109000100-aade96ab11002661f56d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vo-9413000200-e1ce742ceaf03059975f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-9016000000-424ba6a90892708a14cf	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9001000000-8a6e32c88ea68bc7ed3e	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-81555154edd536dba74a	2015-09-16	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45479267

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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

Showing metabocard for O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate (MMDBc0031625)

MOL for #<Metabolite:0x00007fecc18de6a8>

3D MOL for #<Metabolite:0x00007fecc18de6a8>

3D SDF for #<Metabolite:0x00007fecc18de6a8>

3D-SDF for #<Metabolite:0x00007fecc18de6a8>

PDB for #<Metabolite:0x00007fecc18de6a8>

3D PDB for #<Metabolite:0x00007fecc18de6a8>

SMILES for #<Metabolite:0x00007fecc18de6a8>

INCHI for #<Metabolite:0x00007fecc18de6a8>

Structure for #<Metabolite:0x00007fecc18de6a8>

3D Structure for #<Metabolite:0x00007fecc18de6a8>