MiMeDB: Showing metabocard for UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine (MMDBc0030106)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:54:06 UTC

Update Date

2022-08-31 17:39:45 UTC

Metabolite ID

MMDBc0030106

Metabolite Identification

Common Name

UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine

Description

UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. UDP-MurNAc-pentapeptide is a peptidoglycan precursor. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at 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-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred 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. UDP-MurNAc-pentapeptide is a feedback inhibitor of UDP-MurNAc-peptide synthesis. (PMID 357424 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10231213492D          

 92 94  0  0  0  0            999 V2000
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M  END


  Mrv0541 10231213492D          

 92 94  0  0  0  0            999 V2000
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703    8.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    6.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.7752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    5.6745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.6817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    5.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016    6.9155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    7.7796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  2  0  0  0  0
 16  1  1  1  0  0  0
 17  2  1  6  0  0  0
 18  3  1  6  0  0  0
 19  4  1  0  0  0  0
 20  5  1  4  0  0  0
 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 23 14  1  1  0  0  0
 24 15  1  1  0  0  0
 25 10  1  0  0  0  0
 26 11  1  0  0  0  0
 28 24  1  0  0  0  0
 29 23  1  0  0  0  0
 30 28  1  0  0  0  0
 31 27  1  0  0  0  0
 31 29  1  0  0  0  0
 32 16  1  0  0  0  0
 33 17  1  0  0  0  0
 34 19  1  0  0  0  0
 35 21  1  0  0  0  0
 36 30  1  0  0  0  0
 37 18  1  0  0  0  0
 38 22  1  0  0  0  0
 39 27  1  0  0  0  0
 41 12  1  0  0  0  0
 42 17  1  0  0  0  0
 42 34  2  0  0  0  0
 43 16  1  0  0  0  0
 43 35  2  0  0  0  0
 44 18  1  0  0  0  0
 44 32  2  0  0  0  0
 45 20  2  0  0  0  0
 27 45  1  6  0  0  0
 21 46  1  6  0  0  0
 46 25  2  0  0  0  0
 47 22  1  4  0  0  0
 47 33  2  0  0  0  0
 48 26  2  0  0  0  0
 48 40  1  0  0  0  0
 49 13  1  0  0  0  0
 36 49  1  1  0  0  0
 49 40  1  0  0  0  0
 50 14  1  0  0  0  0
 51 20  1  0  0  0  0
 25 52  1  4  0  0  0
 53 26  1  0  0  0  0
 28 54  1  6  0  0  0
 29 55  1  6  0  0  0
 30 56  1  6  0  0  0
 32 57  1  4  0  0  0
 58 33  1  0  0  0  0
 34 59  1  4  0  0  0
 35 60  1  4  0  0  0
 61 37  2  0  0  0  0
 62 37  1  0  0  0  0
 63 38  2  0  0  0  0
 64 38  1  0  0  0  0
 65 40  2  0  0  0  0
 70 15  1  0  0  0  0
 71 19  1  0  0  0  0
 31 71  1  1  0  0  0
 72 24  1  0  0  0  0
 72 36  1  0  0  0  0
 73 23  1  0  0  0  0
 73 39  1  0  0  0  0
 74 39  1  0  0  0  0
 76 66  1  0  0  0  0
 76 67  2  0  0  0  0
 76 70  1  0  0  0  0
 76 75  1  0  0  0  0
 77 68  1  0  0  0  0
 77 69  2  0  0  0  0
 77 74  1  0  0  0  0
 77 75  1  0  0  0  0
 16 78  1  6  0  0  0
 17 79  1  1  0  0  0
 18 80  1  1  0  0  0
 81 19  1  0  0  0  0
 21 82  1  6  0  0  0
 83 22  1  0  0  0  0
 23 84  1  6  0  0  0
 24 85  1  6  0  0  0
 27 86  1  1  0  0  0
 28 87  1  1  0  0  0
 29 88  1  1  0  0  0
 30 89  1  1  0  0  0
 31 90  1  6  0  0  0
 36 91  1  6  0  0  0
 92 39  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030106

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=N[C@@]([H])(C)C(O)=NC([H])(CCC(O)=N[C@@]([H])(CCCCN)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/t16-,17+,18-,19?,21+,22?,23-,24-,27-,28-,29-,30-,31-,36-,39?/m1/s1

> <INCHI_KEY>
PFMVORMCVGOQKR-FQSOPKRZSA-N

> <FORMULA>
C40H65N9O26P2

> <MOLECULAR_WEIGHT>
1149.9363

> <EXACT_MASS>
1149.351596321

> <JCHEM_ACCEPTOR_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
106.12293432468138

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoic acid

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-3.725663718947443

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.7944461147899182

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7121637935196965

> <JCHEM_PKA_STRONGEST_BASIC>
10.205490304515552

> <JCHEM_POLAR_SURFACE_AREA>
559.9600000000002

> <JCHEM_REFRACTIVITY>
250.9283000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-OCT-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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+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+0
HETATM   75  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   76  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   77  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   78  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   81  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   82  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   83  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   85  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   86  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   87  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   88  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   89  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   92  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6    7    8                                                       
CONECT    7    6   12                                                       
CONECT    8    6   21                                                       
CONECT    9   10   22                                                       
CONECT   10    9   25                                                       
CONECT   11   13   26                                                       
CONECT   12    7   41                                                       
CONECT   13   11   49                                                       
CONECT   14   23   50                                                       
CONECT   15   24   70                                                       
CONECT   16    1   32   43   78                                             
CONECT   17    2   33   42   79                                             
CONECT   18    3   37   44   80                                             
CONECT   19    4   34   71   81                                             
CONECT   20    5   45   51                                                  
CONECT   21    8   35   46   82                                             
CONECT   22    9   38   47   83                                             
CONECT   23   14   29   73   84                                             
CONECT   24   15   28   72   85                                             
CONECT   25   10   46   52                                                  
CONECT   26   11   48   53                                                  
CONECT   27   31   39   45   86                                             
CONECT   28   24   30   54   87                                             
CONECT   29   23   31   55   88                                             
CONECT   30   28   36   56   89                                             
CONECT   31   27   29   71   90                                             
CONECT   32   16   44   57                                                  
CONECT   33   17   47   58                                                  
CONECT   34   19   42   59                                                  
CONECT   35   21   43   60                                                  
CONECT   36   30   49   72   91                                             
CONECT   37   18   61   62                                                  
CONECT   38   22   63   64                                                  
CONECT   39   27   73   74   92                                             
CONECT   40   48   49   65                                                  
CONECT   41   12                                                            
CONECT   42   17   34                                                       
CONECT   43   16   35                                                       
CONECT   44   18   32                                                       
CONECT   45   20   27                                                       
CONECT   46   21   25                                                       
CONECT   47   22   33                                                       
CONECT   48   26   40                                                       
CONECT   49   13   36   40                                                  
CONECT   50   14                                                            
CONECT   51   20                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
CONECT   60   35                                                            
CONECT   61   37                                                            
CONECT   62   37                                                            
CONECT   63   38                                                            
CONECT   64   38                                                            
CONECT   65   40                                                            
CONECT   66   76                                                            
CONECT   67   76                                                            
CONECT   68   77                                                            
CONECT   69   77                                                            
CONECT   70   15   76                                                       
CONECT   71   19   31                                                       
CONECT   72   24   36                                                       
CONECT   73   23   39                                                       
CONECT   74   39   77                                                       
CONECT   75   76   77                                                       
CONECT   76   66   67   70   75                                             
CONECT   77   68   69   74   75                                             
CONECT   78   16                                                            
CONECT   79   17                                                            
CONECT   80   18                                                            
CONECT   81   19                                                            
CONECT   82   21                                                            
CONECT   83   22                                                            
CONECT   84   23                                                            
CONECT   85   24                                                            
CONECT   86   27                                                            
CONECT   87   28                                                            
CONECT   88   29                                                            
CONECT   89   30                                                            
CONECT   90   31                                                            
CONECT   91   36                                                            
CONECT   92   39                                                            
MASTER        0    0    0    0    0    0    0    0   92    0  188    0
END

Synonyms

Value

Source

4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoate

Generator

Molecular Formula

C₄₀H₆₅N₉O₂₆P₂

Average Mass

1149.9363

Monoisotopic Mass

1149.351596321

IUPAC Name

Traditional Name

4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoic acid

CAS Registry Number

Not Available

SMILES

[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=N[C@@]([H])(C)C(O)=NC([H])(CCC(O)=N[C@@]([H])(CCCCN)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/t16-,17+,18-,19?,21+,22?,23-,24-,27-,28-,29-,30-,31-,36-,39?/m1/s1

InChI Key

PFMVORMCVGOQKR-FQSOPKRZSA-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
Alpha-oligopeptide
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
Alpha peptide
Saccharolipid
Glutamine or derivatives
N-acyl-alpha-hexosamine
Disaccharide phosphate
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alanine or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
L-alpha-amino acid
Organic pyrophosphate
Isoprenoid phosphate
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid
Medium-chain fatty acid
Monoalkyl phosphate
Hydroxy fatty acid
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Acetamide
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Acetal
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	0.2 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-3.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	31	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	559.96 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	250.93 m³·mol⁻¹	ChemAxon
Polarizability	106.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1900100000-ca60f48eab121e478fd8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000100-5f1cabf69b348c6629aa	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-6921100001-9b4fc4ff9dae58b61f10	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-5901100100-e2f2c32dccc7d77d95a4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-4903100002-39705f2f3e29d8e03294	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-4913011000-3d8817522bb28cc942c2	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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

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

42626415

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ishiguro EE, Ramey WD: Involvement of the relA gene product and feedback inhibition in the regulation of DUP-N-acetylmuramyl-peptide synthesis in Escherichia coli. J Bacteriol. 1978 Sep;135(3):766-74. doi: 10.1128/jb.135.3.766-774.1978. [PubMed:357424 ]
van der Werf MJ, Overkamp KM, Muilwijk B, Coulier L, Hankemeier T: Microbial metabolomics: toward a platform with full metabolome coverage. Anal Biochem. 2007 Nov 1;370(1):17-25. doi: 10.1016/j.ab.2007.07.022. Epub 2007 Aug 1. [PubMed:17765195 ]
Winder CL, Dunn WB, Schuler S, Broadhurst D, Jarvis R, Stephens GM, Goodacre R: Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites. Anal Chem. 2008 Apr 15;80(8):2939-48. doi: 10.1021/ac7023409. Epub 2008 Mar 11. [PubMed:18331064 ]
Kanehisa M, Goto S, Sato Y, Furumichi M, Tanabe M: KEGG for integration and interpretation of large-scale molecular data sets. Nucleic Acids Res. 2012 Jan;40(Database issue):D109-14. doi: 10.1093/nar/gkr988. Epub 2011 Nov 10. [PubMed:22080510 ]

Showing metabocard for UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine (MMDBc0030106)

MOL for #<Metabolite:0x00007fdaf7503ac8>

3D MOL for #<Metabolite:0x00007fdaf7503ac8>

3D SDF for #<Metabolite:0x00007fdaf7503ac8>

3D-SDF for #<Metabolite:0x00007fdaf7503ac8>

PDB for #<Metabolite:0x00007fdaf7503ac8>

3D PDB for #<Metabolite:0x00007fdaf7503ac8>

SMILES for #<Metabolite:0x00007fdaf7503ac8>

INCHI for #<Metabolite:0x00007fdaf7503ac8>

Structure for #<Metabolite:0x00007fdaf7503ac8>

3D Structure for #<Metabolite:0x00007fdaf7503ac8>