NP-MRD: Showing NP-Card for Muramic acid (NP0000016)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:45 UTC

Updated at

2021-06-29 00:47:43 UTC

NP-MRD ID

NP0000016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Muramic acid

Description

Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. Muramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid is an amino sugar acid. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. In terms of chemical composition, it is the ether of lactic acid and glucosamine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003254
     RDKit          3D
Muramic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.4145   -0.8025    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528    0.2642    0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2418    0.0518   -0.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -0.1577    0.4858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9639    0.8869    0.2679 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5376    2.1164   -0.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9320    0.3596   -0.7806 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8233    1.4888   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.0875   -2.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -0.6359   -0.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.6799    0.3210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3329   -1.9514    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -1.5563    0.2364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0243   -2.0764   -1.0443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9585    1.5638    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    2.3261   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    2.0047    0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801   -1.6752    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.0702   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3649   -0.3798    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    0.2460    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.0821    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593    0.9861    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543    2.1558   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -0.0620   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    2.2656   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    1.9965   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481    1.5936   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.5956   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618   -2.9090    1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -2.2205    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646   -3.0182   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -1.4556   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0478    2.9349    1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 13  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  4 22  1  1
  5 23  1  1
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  6
 12 30  1  0
 13 31  1  1
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  END

Untitled Document-4
  Mrv1652305201900032D          

 17 17  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  2  7  1  6  0  0  0
  3  8  1  6  0  0  0
  4  9  1  6  0  0  0
  1 10  1  1  0  0  0
  5 11  1  1  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O[C@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7+,9-/m1/s1

> <INCHI_KEY>
MSFSPUZXLOGKHJ-LEISLEKSSA-N

> <FORMULA>
C9H17NO7

> <MOLECULAR_WEIGHT>
251.2338

> <EXACT_MASS>
251.100501903

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.419204506721346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-4.614715255918833

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.73613012642159

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.328594007566756

> <JCHEM_PKA_STRONGEST_BASIC>
8.122175144111422

> <JCHEM_POLAR_SURFACE_AREA>
142.47

> <JCHEM_REFRACTIVITY>
52.9106

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003254
     RDKit          3D
Muramic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.4145   -0.8025    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528    0.2642    0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2418    0.0518   -0.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -0.1577    0.4858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9639    0.8869    0.2679 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5376    2.1164   -0.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9320    0.3596   -0.7806 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8233    1.4888   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.0875   -2.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -0.6359   -0.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.6799    0.3210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3329   -1.9514    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -1.5563    0.2364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0243   -2.0764   -1.0443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9585    1.5638    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    2.3261   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    2.0047    0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801   -1.6752    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.0702   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3649   -0.3798    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    0.2460    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.0821    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593    0.9861    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543    2.1558   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -0.0620   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    2.2656   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    1.9965   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481    1.5936   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.5956   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618   -2.9090    1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -2.2205    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646   -3.0182   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -1.4556   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0478    2.9349    1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 13  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  4 22  1  1
  5 23  1  1
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  6
 12 30  1  0
 13 31  1  1
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  END

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-4                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   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       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    3   12                                                       
CONECT    9    4                                                            
CONECT   10    1   17                                                       
CONECT   11    5                                                            
CONECT   12    8   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   10                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0003254
HETATM    1  C1  UNL     1      -3.415  -0.802   0.334  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.353   0.264   0.541  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.242   0.052  -0.245  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.072  -0.158   0.486  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.964   0.887   0.268  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.538   2.116  -0.134  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.932   0.360  -0.781  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.823   1.489  -1.188  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.830   1.088  -2.059  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.658  -0.636  -0.137  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.929  -1.680   0.321  1.00  0.00           C  
HETATM   12  O5  UNL     1       2.333  -1.951   1.649  1.00  0.00           O  
HETATM   13  C8  UNL     1       0.447  -1.556   0.236  1.00  0.00           C  
HETATM   14  N1  UNL     1      -0.024  -2.076  -1.044  1.00  0.00           N  
HETATM   15  C9  UNL     1      -2.958   1.564   0.219  1.00  0.00           C  
HETATM   16  O6  UNL     1      -2.493   2.326  -0.664  1.00  0.00           O  
HETATM   17  O7  UNL     1      -4.094   2.005   0.897  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.180  -1.675   0.977  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.541  -1.070  -0.728  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.365  -0.380   0.724  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.133   0.246   1.627  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.390  -0.082   1.568  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.559   0.986   1.214  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.254   2.156  -1.074  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.440  -0.062  -1.653  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.224   2.266  -1.709  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.294   1.997  -0.317  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.648   1.594  -1.867  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.224  -2.596  -0.254  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.362  -2.909   1.836  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.010  -2.221   1.011  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.465  -3.018  -0.951  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.696  -1.456  -1.512  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.048   2.935   1.332  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   15   21
CONECT    3    4
CONECT    4    5   13   22
CONECT    5    6    7   23
CONECT    6   24
CONECT    7    8   10   25
CONECT    8    9   26   27
CONECT    9   28
CONECT   10   11
CONECT   11   12   13   29
CONECT   12   30
CONECT   13   14   31
CONECT   14   32   33
CONECT   15   16   16   17
CONECT   17   34
END

HMDB0003254
     RDKit          3D
Muramic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.4145   -0.8025    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528    0.2642    0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2418    0.0518   -0.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723   -0.1577    0.4858 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9639    0.8869    0.2679 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5376    2.1164   -0.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9320    0.3596   -0.7806 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8233    1.4888   -1.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299    1.0875   -2.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -0.6359   -0.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -1.6799    0.3210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3329   -1.9514    1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -1.5563    0.2364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0243   -2.0764   -1.0443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9585    1.5638    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4934    2.3261   -0.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940    2.0047    0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801   -1.6752    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.0702   -0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3649   -0.3798    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    0.2460    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.0821    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5593    0.9861    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543    2.1558   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -0.0620   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    2.2656   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    1.9965   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6481    1.5936   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236   -2.5956   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618   -2.9090    1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -2.2205    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4646   -3.0182   -0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -1.4556   -1.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0478    2.9349    1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 13  4  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  4 22  1  1
  5 23  1  1
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  6
 12 30  1  0
 13 31  1  1
 14 32  1  0
 14 33  1  0
 17 34  1  0
M  END

View in JSmol

Synonyms

Value	Source
Muramate	Generator
(+)-Muramate	HMDB
(+)-Muramic acid	HMDB
3-O-alpha-Carboxyethyl-D-glucosamine	HMDB
3-O-alpha-Carboxyethyl-delta-glucosamine	HMDB
Muramic acid hydrate	HMDB
Murexide	HMDB
(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoate	HMDB

Chemical Formula

C₉H₁₇NO₇

Average Mass

251.2338 Da

Monoisotopic Mass

251.10050 Da

IUPAC Name

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

Traditional Name

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

CAS Registry Number

1114-41-6

SMILES

C[C@@H](O[C@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7+,9-/m1/s1

InChI Key

MSFSPUZXLOGKHJ-LEISLEKSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Synechococcus elongatus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Muramic_acid
Hexose monosaccharide
Amino saccharide
Sugar acid
Monosaccharide
Oxane
Amino acid or derivatives
Hemiacetal
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Primary alcohol
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	152 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.6	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	8.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	142.47 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.91 m³·mol⁻¹	ChemAxon
Polarizability	23.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003254

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Muramic acid

METLIN ID

3381

PubChem Compound

22833605

PDB ID

Not Available

ChEBI ID

28118

Good Scents ID

Not Available

References

General References

Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7. [PubMed:7729869 ]
Kozar MP, Krahmer MT, Fox A, Gray BM: Failure To detect muramic acid in normal rat tissues but detection in cerebrospinal fluids from patients with Pneumococcal meningitis. Infect Immun. 2000 Aug;68(8):4688-98. [PubMed:10899874 ]
Fox A, Fox K, Christensson B, Harrelson D, Krahmer M: Absolute identification of muramic acid, at trace levels, in human septic synovial fluids in vivo and absence in aseptic fluids. Infect Immun. 1996 Sep;64(9):3911-5. [PubMed:8751949 ]
Christensson B, Gilbart J, Fox A, Morgan SL: Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids. Arthritis Rheum. 1989 Oct;32(10):1268-72. [PubMed:2679561 ]
Mollner S, Braun V: Murein hydrolase (N-acetyl-muramyl-L-alanine amidase) in human serum. Arch Microbiol. 1984 Dec;140(2-3):171-7. [PubMed:6152147 ]
Chen T, Rimpilainen M, Luukkainen R, Mottonen T, Yli-Jama T, Jalava J, Vainio O, Toivanen P: Bacterial components in the synovial tissue of patients with advanced rheumatoid arthritis or osteoarthritis: analysis with gas chromatography-mass spectrometry and pan-bacterial polymerase chain reaction. Arthritis Rheum. 2003 Jun 15;49(3):328-34. [PubMed:12794787 ]
Bal K, Larsson L: New and simple procedure for the determination of muramic acid in chemically complex environments by gas chromatography-ion trap tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 2000 Jan 28;738(1):57-65. [PubMed:10778926 ]

Showing NP-Card for Muramic acid (NP0000016)

MOL for NP0000016 (Muramic acid)

3D MOL for NP0000016 (Muramic acid)

3D SDF for NP0000016 (Muramic acid)

3D-SDF for NP0000016 (Muramic acid)

PDB for NP0000016 (Muramic acid)

3D PDB for NP0000016 (Muramic acid)

SMILES for NP0000016 (Muramic acid)

INCHI for NP0000016 (Muramic acid)

Structure for NP0000016 (Muramic acid)

3D Structure for NP0000016 (Muramic acid)