MiMeDB: Showing metabocard for Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (MMDBc0030112)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:54:22 UTC

Update Date

2022-08-31 17:39:48 UTC

Metabolite ID

MMDBc0030112

Metabolite Identification

Common Name

Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine

Description

Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is an intermediate in peptidoglycan synthesis. It is a substrate for the enzyme undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase (murG). 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

            
  Mrv1533006031516052D          

119119  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
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117119  1  0  0  0  0
M  CHG  6  11  -1  22  -1  23   1  36  -1  55  -1  59  -1
M  END

            
  Mrv1533006031516052D          

119119  0  0  0  0            999 V2000
  -15.0038    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0038   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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105106  1  0  0  0  0
107106  1  4  0  0  0
107108  2  0  0  0  0
108109  1  0  0  0  0
108110  1  0  0  0  0
110111  1  0  0  0  0
111112  1  0  0  0  0
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117118  2  0  0  0  0
117119  1  0  0  0  0
M  CHG  6  11  -1  22  -1  23   1  36  -1  55  -1  59  -1
M  END
> <DATABASE_ID>
MMDBc0030112

> <DATABASE_NAME>
MIME

> <SMILES>
CC(NC(=O)C(C)NC(=O)C(CCCC([NH3+])C([O-])=O)NC(=O)C(CCC([O-])=O)NC(=O)C(C)NC(=O)C(C)OC1C(O)C(CO)OC(OP([O-])(=O)OP([O-])(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C1NC(C)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C87H143N7O23P2/c1-56(2)29-18-30-57(3)31-19-32-58(4)33-20-34-59(5)35-21-36-60(6)37-22-38-61(7)39-23-40-62(8)41-24-42-63(9)43-25-44-64(10)45-26-46-65(11)47-27-48-66(12)53-54-113-118(109,110)117-119(111,112)116-87-77(92-71(17)96)79(78(99)75(55-95)115-87)114-70(16)82(102)89-68(14)81(101)93-74(51-52-76(97)98)84(104)94-73(50-28-49-72(88)86(107)108)83(103)90-67(13)80(100)91-69(15)85(105)106/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,99H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,102)(H,90,103)(H,91,100)(H,92,96)(H,93,101)(H,94,104)(H,97,98)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/p-4

> <INCHI_KEY>
QSVYTJPCVMYPIS-UHFFFAOYSA-J

> <FORMULA>
C87H139N7O23P2

> <MOLECULAR_WEIGHT>
1713.045

> <EXACT_MASS>
1711.941952079

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
258

> <JCHEM_AVERAGE_POLARIZABILITY>
192.34253072112588

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-azaniumyl-6-{4-carboxylato-2-[2-(2-{[3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-({[(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]phosphinato}oxy)oxan-4-yl]oxy}propanamido)propanamido]butanamido}-6-({1-[(1-carboxylatoethyl)carbamoyl]ethyl}carbamoyl)hexanoate

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
10.191286910856629

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.0638820228324564

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4812888621752847

> <JCHEM_PKA_STRONGEST_BASIC>
9.524002664274034

> <JCHEM_POLAR_SURFACE_AREA>
489.50000000000006

> <JCHEM_REFRACTIVITY>
507.70689999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
60

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ammonio-6-{4-carboxylato-2-[2-(2-{[3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-{[(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)oxyphosphinato]oxy}oxan-4-yl]oxy}propanamido)propanamido]butanamido}-6-({1-[(1-carboxylatoethyl)carbamoyl]ethyl}carbamoyl)hexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-15         0                                  
HETATM    1  C   UNK     0     -28.007   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -28.007  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -29.341  -1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -29.341  -3.080   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0     -30.675  -0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0     -32.008  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -32.008  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -33.342  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -32.008  -6.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0     -34.676  -6.160   0.000  0.00  0.00           O-1
HETATM   12  C   UNK     0     -33.342  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -33.342   0.770   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0     -34.676  -1.540   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0     -36.009  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -36.009   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -34.676   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -34.676   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -33.342   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -33.342   5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -34.676   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -32.008   6.160   0.000  0.00  0.00           O-1
HETATM   23  N   UNK     0     -32.008   3.080   0.000  0.00  0.00           N+1
HETATM   24  C   UNK     0     -37.343  -1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -37.343  -3.080   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0     -38.677  -0.770   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0     -40.010  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -40.010  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -41.344  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -41.344   0.770   0.000  0.00  0.00           O+0
HETATM   31  N   UNK     0     -42.678  -1.540   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0     -44.011  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -44.011   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -45.345  -1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -46.679  -0.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -45.345  -3.080   0.000  0.00  0.00           O-1
HETATM   37  N   UNK     0     -26.674  -1.540   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0     -25.340  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -25.340   0.770   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -22.673  -0.770   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0     -21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -18.671  -1.540   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -18.671  -3.080   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0     -20.005  -3.850   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0     -22.673  -3.850   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0     -20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -21.339  -6.160   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   53  P   UNK     0     -16.004  -1.540   0.000  0.00  0.00           P+0
HETATM   54  O   UNK     0     -16.774  -2.874   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0     -15.234  -0.206   0.000  0.00  0.00           O-1
HETATM   56  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   57  P   UNK     0     -13.337  -1.540   0.000  0.00  0.00           P+0
HETATM   58  O   UNK     0     -12.567  -2.874   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0     -14.107  -0.206   0.000  0.00  0.00           O-1
HETATM   60  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0     -10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      18.671  -1.540   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      18.671  -3.080   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      25.340  -0.770   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      26.674  -1.540   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      28.007  -0.770   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      30.675  -0.770   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      32.008  -1.540   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      33.342  -0.770   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      34.676  -1.540   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      34.676  -3.080   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      36.009  -0.770   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      37.343  -1.540   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      38.677  -0.770   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      40.010  -1.540   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0      40.010  -3.080   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0      41.344  -0.770   0.000  0.00  0.00           C+0
HETATM  111  C   UNK     0      42.678  -1.540   0.000  0.00  0.00           C+0
HETATM  112  C   UNK     0      44.011  -0.770   0.000  0.00  0.00           C+0
HETATM  113  C   UNK     0      45.345  -1.540   0.000  0.00  0.00           C+0
HETATM  114  C   UNK     0      46.679  -0.770   0.000  0.00  0.00           C+0
HETATM  115  C   UNK     0      45.345  -3.080   0.000  0.00  0.00           C+0
HETATM  116  N   UNK     0     -20.005   0.770   0.000  0.00  0.00           N+0
HETATM  117  C   UNK     0     -21.339   1.540   0.000  0.00  0.00           C+0
HETATM  118  O   UNK     0     -22.673   0.770   0.000  0.00  0.00           O+0
HETATM  119  C   UNK     0     -21.339   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19                                                            
CONECT   24   15   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    2   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45  116                                                  
CONECT   45   44   46   52                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   50                                                  
CONECT   48   47   43   49                                                  
CONECT   49   48                                                            
CONECT   50   47   51                                                       
CONECT   51   50                                                            
CONECT   52   45   53                                                       
CONECT   53   52   54   55   56                                             
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   53   57                                                       
CONECT   57   56   58   59   60                                             
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60   57   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79   80                                                  
CONECT   79   78                                                            
CONECT   80   78   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84   85                                                  
CONECT   84   83                                                            
CONECT   85   83   86                                                       
CONECT   86   85   87                                                       
CONECT   87   86   88                                                       
CONECT   88   87   89   90                                                  
CONECT   89   88                                                            
CONECT   90   88   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94   95                                                  
CONECT   94   93                                                            
CONECT   95   93   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99  100                                                  
CONECT   99   98                                                            
CONECT  100   98  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101  103                                                       
CONECT  103  102  104  105                                                  
CONECT  104  103                                                            
CONECT  105  103  106                                                       
CONECT  106  105  107                                                       
CONECT  107  106  108                                                       
CONECT  108  107  109  110                                                  
CONECT  109  108                                                            
CONECT  110  108  111                                                       
CONECT  111  110  112                                                       
CONECT  112  111  113                                                       
CONECT  113  112  114  115                                                  
CONECT  114  113                                                            
CONECT  115  113                                                            
CONECT  116   44  117                                                       
CONECT  117  116  118  119                                                  
CONECT  118  117                                                            
CONECT  119  117                                                            
MASTER        0    0    0    0    0    0    0    0  119    0  238    0
END

Synonyms

Not Available

Molecular Formula

C₈₇H₁₃₉N₇O₂₃P₂

Average Mass

1713.045

Monoisotopic Mass

1711.941952079

IUPAC Name

2-azaniumyl-6-{4-carboxylato-2-[2-(2-{[3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-({[(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]phosphinato}oxy)oxan-4-yl]oxy}propanamido)propanamido]butanamido}-6-({1-[(1-carboxylatoethyl)carbamoyl]ethyl}carbamoyl)hexanoate

Traditional Name

2-ammonio-6-{4-carboxylato-2-[2-(2-{[3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-{[(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)oxyphosphinato]oxy}oxan-4-yl]oxy}propanamido)propanamido]butanamido}-6-({1-[(1-carboxylatoethyl)carbamoyl]ethyl}carbamoyl)hexanoate

CAS Registry Number

Not Available

SMILES

CC(NC(=O)C(C)NC(=O)C(CCCC([NH3+])C([O-])=O)NC(=O)C(CCC([O-])=O)NC(=O)C(C)NC(=O)C(C)OC1C(O)C(CO)OC(OP([O-])(=O)OP([O-])(=O)OCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C1NC(C)=O)C([O-])=O

InChI Identifier

InChI=1S/C87H143N7O23P2/c1-56(2)29-18-30-57(3)31-19-32-58(4)33-20-34-59(5)35-21-36-60(6)37-22-38-61(7)39-23-40-62(8)41-24-42-63(9)43-25-44-64(10)45-26-46-65(11)47-27-48-66(12)53-54-113-118(109,110)117-119(111,112)116-87-77(92-71(17)96)79(78(99)75(55-95)115-87)114-70(16)82(102)89-68(14)81(101)93-74(51-52-76(97)98)84(104)94-73(50-28-49-72(88)86(107)108)83(103)90-67(13)80(100)91-69(15)85(105)106/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,99H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,102)(H,90,103)(H,91,100)(H,92,96)(H,93,101)(H,94,104)(H,97,98)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/p-4

InChI Key

QSVYTJPCVMYPIS-UHFFFAOYSA-J

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
Alpha peptide
N-acyl-alpha-hexosamine
N-acyl-alpha amino acid or derivatives
Alanine or derivatives
Organic pyrophosphate
Monosaccharide phosphate
Isoprenoid phosphate
Alpha-amino acid or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Monosaccharide
Amino acid
Secondary alcohol
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
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	0.0015 g/L	ALOGPS
logP	5.19	ALOGPS
logP	10.19	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	489.5 Å²	ChemAxon
Rotatable Bond Count	60	ChemAxon
Refractivity	507.71 m³·mol⁻¹	ChemAxon
Polarizability	192.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

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

Exposure Sources

Host Biospecimen and Location

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74413809

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 Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine (MMDBc0030112)

MOL for #<Metabolite:0x00007fdb44bea9e8>

3D MOL for #<Metabolite:0x00007fdb44bea9e8>

3D SDF for #<Metabolite:0x00007fdb44bea9e8>

3D-SDF for #<Metabolite:0x00007fdb44bea9e8>

PDB for #<Metabolite:0x00007fdb44bea9e8>

3D PDB for #<Metabolite:0x00007fdb44bea9e8>

SMILES for #<Metabolite:0x00007fdb44bea9e8>

INCHI for #<Metabolite:0x00007fdb44bea9e8>

Structure for #<Metabolite:0x00007fdb44bea9e8>

3D Structure for #<Metabolite:0x00007fdb44bea9e8>