MiMeDB: Showing metabocard for N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol (MMDBc0030126)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:54:55 UTC

Update Date

2022-08-31 17:39:54 UTC

Metabolite ID

MMDBc0030126

Metabolite Identification

Common Name

N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol

Description

N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol 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.Glycosyltransferase MurG catalyses the transfer of N-acetyl-d-glucosamine to lipid intermediate I on the bacterial peptidoglycan biosynthesis pathway, and is a target for development of new antibacterial agents. (PMID 20226679 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08131209362D          

131131  0  0  0  0            999 V2000
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M  END


  Mrv0541 08131209362D          

131131  0  0  0  0            999 V2000
   -0.7145   29.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
MMDBc0030126

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](N)(CCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(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)[C@]1([H])N=C(C)O)C(O)=O)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=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(98)75(55-95)115-87)114-70(16)82(101)89-68(14)81(100)94-74(86(107)108)51-52-76(97)93-73(50-28-49-72(88)85(105)106)83(102)90-67(13)80(99)91-69(15)84(103)104/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,98H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,101)(H,90,102)(H,91,99)(H,92,96)(H,93,97)(H,94,100)(H,103,104)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/t67-,68+,69-,70-,72-,73+,74-,75-,77-,78-,79-,87+/m1/s1

> <INCHI_KEY>
PNWZQTONLRRPST-OPZGOLSISA-N

> <FORMULA>
C87H143N7O23P2

> <MOLECULAR_WEIGHT>
1717.0469

> <EXACT_MASS>
1715.971056941

> <JCHEM_ACCEPTOR_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
191.18509220421294

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-{[hydroxy({hydroxy[(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)oxy]phosphoryl}oxy)phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
16.700202672666666

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.8821575056523585

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7155944188550754

> <JCHEM_POLAR_SURFACE_AREA>
494.6700000000001

> <JCHEM_REFRACTIVITY>
469.27639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
60

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-({hydroxy[hydroxy(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)oxyphosphoryl]oxyphosphoryl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   88  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   89  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   90  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   91  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   92  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   93  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   94  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   95  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  102  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  103  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  104  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  106  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  107  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  108  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  109  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  113  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  114  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  115  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  116  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  117  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM  118  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM  119  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM  120  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  121  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  122  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  123  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  124  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  125  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  126  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  127  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  128  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  129  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  130  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  131  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   56                                                            
CONECT    2   56                                                            
CONECT    3   57                                                            
CONECT    4   58                                                            
CONECT    5   59                                                            
CONECT    6   60                                                            
CONECT    7   61                                                            
CONECT    8   62                                                            
CONECT    9   63                                                            
CONECT   10   64                                                            
CONECT   11   65                                                            
CONECT   12   66                                                            
CONECT   13   67                                                            
CONECT   14   68                                                            
CONECT   15   69                                                            
CONECT   16   70                                                            
CONECT   17   71                                                            
CONECT   18   29   30                                                       
CONECT   19   31   32                                                       
CONECT   20   33   34                                                       
CONECT   21   35   36                                                       
CONECT   22   37   38                                                       
CONECT   23   39   40                                                       
CONECT   24   41   42                                                       
CONECT   25   43   44                                                       
CONECT   26   45   46                                                       
CONECT   27   47   48                                                       
CONECT   28   49   50                                                       
CONECT   29   18   56                                                       
CONECT   30   18   57                                                       
CONECT   31   19   57                                                       
CONECT   32   19   58                                                       
CONECT   33   20   58                                                       
CONECT   34   20   59                                                       
CONECT   35   21   59                                                       
CONECT   36   21   60                                                       
CONECT   37   22   60                                                       
CONECT   38   22   61                                                       
CONECT   39   23   61                                                       
CONECT   40   23   62                                                       
CONECT   41   24   62                                                       
CONECT   42   24   63                                                       
CONECT   43   25   63                                                       
CONECT   44   25   64                                                       
CONECT   45   26   64                                                       
CONECT   46   26   65                                                       
CONECT   47   27   65                                                       
CONECT   48   27   66                                                       
CONECT   49   28   72                                                       
CONECT   50   28   73                                                       
CONECT   51   52   74                                                       
CONECT   52   51   76                                                       
CONECT   53   54   66                                                       
CONECT   54   53  113                                                       
CONECT   55   75   95                                                       
CONECT   56    1    2   29                                                  
CONECT   57    3   30   31                                                  
CONECT   58    4   32   33                                                  
CONECT   59    5   34   35                                                  
CONECT   60    6   36   37                                                  
CONECT   61    7   38   39                                                  
CONECT   62    8   40   41                                                  
CONECT   63    9   42   43                                                  
CONECT   64   10   44   45                                                  
CONECT   65   11   46   47                                                  
CONECT   66   12   48   53                                                  
CONECT   67   13   80   90  120                                             
CONECT   68   14   81   89  121                                             
CONECT   69   15   84   91  122                                             
CONECT   70   16   82  114  123                                             
CONECT   71   17   92   96                                                  
CONECT   72   49   85   88  124                                             
CONECT   73   50   83   93  125                                             
CONECT   74   51   86   94  126                                             
CONECT   75   55   78  115  127                                             
CONECT   76   52   93   97                                                  
CONECT   77   79   87   92  128                                             
CONECT   78   75   79   98  129                                             
CONECT   79   77   78  114  130                                             
CONECT   80   67   91   99                                                  
CONECT   81   68   94  100                                                  
CONECT   82   70   89  101                                                  
CONECT   83   73   90  102                                                  
CONECT   84   69  103  104                                                  
CONECT   85   72  105  106                                                  
CONECT   86   74  107  108                                                  
CONECT   87   77  115  116  131                                             
CONECT   88   72                                                            
CONECT   89   68   82                                                       
CONECT   90   67   83                                                       
CONECT   91   69   80                                                       
CONECT   92   71   77                                                       
CONECT   93   73   76                                                       
CONECT   94   74   81                                                       
CONECT   95   55                                                            
CONECT   96   71                                                            
CONECT   97   76                                                            
CONECT   98   78                                                            
CONECT   99   80                                                            
CONECT  100   81                                                            
CONECT  101   82                                                            
CONECT  102   83                                                            
CONECT  103   84                                                            
CONECT  104   84                                                            
CONECT  105   85                                                            
CONECT  106   85                                                            
CONECT  107   86                                                            
CONECT  108   86                                                            
CONECT  109  118                                                            
CONECT  110  118                                                            
CONECT  111  119                                                            
CONECT  112  119                                                            
CONECT  113   54  118                                                       
CONECT  114   70   79                                                       
CONECT  115   75   87                                                       
CONECT  116   87  119                                                       
CONECT  117  118  119                                                       
CONECT  118  109  110  113  117                                             
CONECT  119  111  112  116  117                                             
CONECT  120   67                                                            
CONECT  121   68                                                            
CONECT  122   69                                                            
CONECT  123   70                                                            
CONECT  124   72                                                            
CONECT  125   73                                                            
CONECT  126   74                                                            
CONECT  127   75                                                            
CONECT  128   77                                                            
CONECT  129   78                                                            
CONECT  130   79                                                            
CONECT  131   87                                                            
MASTER        0    0    0    0    0    0    0    0  131    0  262    0
END

Synonyms

Not Available

Molecular Formula

C₈₇H₁₄₃N₇O₂₃P₂

Average Mass

1717.0469

Monoisotopic Mass

1715.971056941

IUPAC Name

(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-{[hydroxy({hydroxy[(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)oxy]phosphoryl}oxy)phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid

Traditional Name

(2R,6S)-2-amino-6-{[(4R)-4-carboxy-1-hydroxy-4-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5R,6S)-3-hydroxy-6-({hydroxy[hydroxy(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)oxyphosphoryl]oxyphosphoryl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](N)(CCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(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)[C@]1([H])N=C(C)O)C(O)=O)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=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(98)75(55-95)115-87)114-70(16)82(101)89-68(14)81(100)94-74(86(107)108)51-52-76(97)93-73(50-28-49-72(88)85(105)106)83(102)90-67(13)80(99)91-69(15)84(103)104/h29,31,33,35,37,39,41,43,45,47,53,67-70,72-75,77-79,87,95,98H,18-28,30,32,34,36,38,40,42,44,46,48-52,54-55,88H2,1-17H3,(H,89,101)(H,90,102)(H,91,99)(H,92,96)(H,93,97)(H,94,100)(H,103,104)(H,105,106)(H,107,108)(H,109,110)(H,111,112)/t67-,68+,69-,70-,72-,73+,74-,75-,77-,78-,79-,87+/m1/s1

InChI Key

PNWZQTONLRRPST-OPZGOLSISA-N

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
N-acyl-alpha-amino acid
Hexose monosaccharide
Alanine or derivatives
D-alpha-amino acid
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
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic 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
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	0.0019 g/L	ALOGPS
logP	3.71	ALOGPS
logP	16.7	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	27	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	494.67 Å²	ChemAxon
Rotatable Bond Count	60	ChemAxon
Refractivity	469.28 m³·mol⁻¹	ChemAxon
Polarizability	191.19 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1011139200-a5086b1fa04a83dc0d2b	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-3130033911-ab862a3d1358e36e1757	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001d-9333332400-1bd354ac67fc3da0fbdc	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06vj-3000039507-bfb6f7440faf705b9965	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-3300018109-4bce894814e4eb3aa402	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-6910002002-df1a7b3aba2e08f6af47	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019272	Uridine diphosphate-N-acetylglucosamine	Hydrogen Ion	UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase	Transfer of UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine	PathBank	31602464
MMDBr0019276	N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine	Uridine 5'-monophosphate	Phospho-N-acetylmuramoyl-pentapeptide-transferase	Transfer of phospho-N-acetylmuramoyl-pentapeptide	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

25200588

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 N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol (MMDBc0030126)

MOL for #<Metabolite:0x00007fa4e4039068>

3D MOL for #<Metabolite:0x00007fa4e4039068>

3D SDF for #<Metabolite:0x00007fa4e4039068>

3D-SDF for #<Metabolite:0x00007fa4e4039068>

PDB for #<Metabolite:0x00007fa4e4039068>

3D PDB for #<Metabolite:0x00007fa4e4039068>

SMILES for #<Metabolite:0x00007fa4e4039068>

INCHI for #<Metabolite:0x00007fa4e4039068>

Structure for #<Metabolite:0x00007fa4e4039068>

3D Structure for #<Metabolite:0x00007fa4e4039068>