MiMeDB: Showing metabocard for N-Acetylmannosamine (MMDBc0000181)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:50 UTC

Update Date

2024-04-30 19:31:22 UTC

Metabolite ID

MMDBc0000181

Metabolite Identification

Common Name

N-Acetylmannosamine

Description

N-Acetylmannosamine is a monosaccharide that is used as a precursor in the chemical or enzymatic synthesis of the neuraminic acids found in glycolipids and glycoproteins. N-Acetyl-D-mannosamine (ManNAc) is a specific substrate for the synthesis of N-acetylneuraminic acid, the essential precursor of bacterial capsular polysialic acid (PA). N-Acetyl-D-mannosamine is used for the synthesis of sialic acid. It is also a synthetic intermediate for a number of carbohydrate-derived families of biologically active compounds and pharmaceutical candidates. N-Acetylmannosamine is a microbial metabolite of Escherichia (PMID: 7772033 ).

Structure

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

HMDB0001129
     RDKit          3D
N-Acetylmannosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.0368   -0.5508    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.2787    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819    1.2671   -0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102    0.0057    0.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.8604   -0.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3286    1.4961    0.4228 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2163    2.4269    1.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012    0.5322    1.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -0.0481    0.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.8081    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.0685    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -0.8905   -0.7623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7399   -1.6760   -1.6508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    0.0464   -1.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7394   -0.6157   -2.3813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -1.4661    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8569   -0.8185    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    0.0477    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -0.8365    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058    1.6660   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445    2.0404   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520    3.2496    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    0.7637   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -1.1582   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.6624    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4782    0.5744    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -1.5436   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.6109   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    0.7769   -2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209   -1.4154   -1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  6
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END


  Mrv1652304202022152D          

 15 15  0  0  1  0            999 V2000
   11.6179   -5.5067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6179   -6.3317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9034   -5.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9034   -6.7442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1889   -5.5067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1889   -6.3317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3324   -5.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3324   -6.7442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9034   -7.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4743   -6.7442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4743   -5.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7600   -5.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3324   -7.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0468   -7.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6179   -7.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  1  0  0  0
  2  8  1  1  0  0  0
  4  9  1  1  0  0  0
  6 10  1  6  0  0  0
  5 11  1  1  0  0  0
 12 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000181

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8-/m1/s1

> <INCHI_KEY>
OVRNDRQMDRJTHS-OZRXBMAMSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.823604022027684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

> <ALOGPS_LOGP>
-2.60

> <JCHEM_LOGP>
-3.220574411666667

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.811681816700894

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.604129514800414

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5720778168170417

> <JCHEM_POLAR_SURFACE_AREA>
119.25000000000001

> <JCHEM_REFRACTIVITY>
47.024699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylmannosamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001129
     RDKit          3D
N-Acetylmannosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.0368   -0.5508    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.2787    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819    1.2671   -0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102    0.0057    0.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.8604   -0.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3286    1.4961    0.4228 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2163    2.4269    1.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012    0.5322    1.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -0.0481    0.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.8081    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.0685    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -0.8905   -0.7623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7399   -1.6760   -1.6508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    0.0464   -1.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7394   -0.6157   -2.3813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -1.4661    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8569   -0.8185    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    0.0477    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -0.8365    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058    1.6660   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445    2.0404   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520    3.2496    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    0.7637   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -1.1582   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.6624    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4782    0.5744    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -1.5436   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.6109   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    0.7769   -2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209   -1.4154   -1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  6
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      21.687 -10.279   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.687 -11.819   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.353  -9.509   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      20.353 -12.589   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.019 -10.279   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.019 -11.819   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      23.020  -9.509   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      23.020 -12.589   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      20.353 -14.129   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.685 -12.589   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.685  -9.509   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.352 -10.279   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      23.020 -14.129   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.354 -14.899   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.687 -14.899   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6   11                                                  
CONECT    6    4    5   10                                                  
CONECT    7    1                                                            
CONECT    8    2   13                                                       
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    5   12                                                       
CONECT   12   11                                                            
CONECT   13   14   15    8                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0001129
HETATM    1  C1  UNL     1       4.037  -0.551   0.751  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.999   0.279   0.089  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.382   1.267  -0.579  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.610   0.006   0.178  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.687   0.860  -0.493  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.329   1.496   0.423  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.216   2.427   1.282  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.101   0.532   1.095  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.908  -0.048   0.110  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.064  -0.808   0.703  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.841   0.069   1.450  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.032  -0.891  -0.762  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.740  -1.676  -1.651  1.00  0.00           O  
HETATM   14  C8  UNL     1      -0.101   0.046  -1.521  1.00  0.00           C  
HETATM   15  O6  UNL     1       0.739  -0.616  -2.381  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.638  -1.466   1.200  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.857  -0.818   0.053  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.503   0.048   1.561  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.307  -0.837   0.749  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.206   1.666  -1.022  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.045   2.040  -0.240  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.352   3.250   1.359  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.334   0.764  -0.525  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.690  -1.158  -0.143  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.766  -1.662   1.313  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.478   0.574   0.869  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.397  -1.544  -0.128  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.380  -2.611  -1.686  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.746   0.777  -2.049  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.121  -1.415  -1.946  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   14   20
CONECT    6    7    8   21
CONECT    7   22
CONECT    8    9
CONECT    9   10   12   23
CONECT   10   11   24   25
CONECT   11   26
CONECT   12   13   14   27
CONECT   13   28
CONECT   14   15   29
CONECT   15   30
END

HMDB0001129
     RDKit          3D
N-Acetylmannosamine
 30 30  0  0  0  0  0  0  0  0999 V2000
    4.0368   -0.5508    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9987    0.2787    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819    1.2671   -0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102    0.0057    0.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.8604   -0.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3286    1.4961    0.4228 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2163    2.4269    1.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012    0.5322    1.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -0.0481    0.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0640   -0.8081    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407    0.0685    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -0.8905   -0.7623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7399   -1.6760   -1.6508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    0.0464   -1.5208 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7394   -0.6157   -2.3813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -1.4661    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8569   -0.8185    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    0.0477    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -0.8365    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058    1.6660   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445    2.0404   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520    3.2496    1.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337    0.7637   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -1.1582   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.6624    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4782    0.5744    0.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -1.5436   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -2.6109   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455    0.7769   -2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209   -1.4154   -1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  6
  7 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  1
 13 28  1  0
 14 29  1  6
 15 30  1  0
M  END

Synonyms

Value	Source
beta-ManNAc	ChEBI
N-Acetyl-beta-mannosamine	ChEBI
b-ManNAc	Generator
Β-mannac	Generator
N-Acetyl-b-mannosamine	Generator
N-Acetyl-β-mannosamine	Generator
2-Acetamido-2-deoxy-D-mannopyranose	HMDB
2-Acetamido-2-deoxy-D-mannose	HMDB
ManNAc	HMDB
N-Acetyl-D-mannosamine	HMDB
N-Acetylmannosamine, (D)-isomer	HMDB
N-Acetylmannosamine, (L)-isomer	HMDB

Molecular Formula

C₈H₁₅NO₆

Average Mass

221.2078

Monoisotopic Mass

221.089937217

IUPAC Name

N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

N-acetylmannosamine

CAS Registry Number

7772-94-3

SMILES

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

InChI Identifier

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8-/m1/s1

InChI Key

OVRNDRQMDRJTHS-OZRXBMAMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-mannosamine (CHEBI:63154 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	20.82 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-00di-1910000000-c54e9f9969c7d963036f	2018-05-25	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-0pvi-1951000000-56398608d2dd4355e1f6	2018-05-25	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)	splash10-0kw0-3940000000-02993315f1b1a700b7ec	2018-05-25	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-0pvi-2941000000-c2e3ada4d3e27dc6890a	2018-05-25	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-7920000000-9991e74281c314048f5e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0007-3331900000-c6fab10d67507eecce65	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004r-0920000000-26c87e12e0c8c5f919b7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9400000000-f0d2f81f4292b627f0ef	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001j-9000000000-fcbf9adb619f826e3cd3	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0390000000-ce54c5d356ec2fc8ab9f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0il0-2950000000-e4e02ffea74d8dfd0810	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9400000000-180503dcc7682bb1753b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-9830000000-a5028d14de09cabbb303	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ac0-9820000000-d3017a9fb13bdc3aa847	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-ce24407926ce180ba365	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h90-9740000000-db880363194a3979c637	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9540000000-a1f7d557237a521d306a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-18eabe9e3d3657888360	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Fibroblasts
Prostate
Skeletal Muscle
Urine

Tissue Locations

Fibroblasts
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192001	Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase	Enzyme	Q9Y223	Homo sapiens
MMDBp0192002	Sialic acid synthase	Enzyme	Q9NR45	Homo sapiens
MMDBp0192003	N-acylglucosamine 2-epimerase	Enzyme	P51606	Homo sapiens
MMDBp0194150	N-acetylneuraminate lyase	Enzyme	Q9BXD5	Homo sapiens
MMDBp0196656	14 kDa phosphohistidine phosphatase	Enzyme	Q9NRX4	Homo sapiens
MMDBp0196890	Myotubularin-related protein 1	Unknown	Q13613
MMDBp0196891	Myotubularin-related protein 2	Unknown	Q13614
MMDBp0196892	Myotubularin-related protein 6	Unknown	Q9Y217
MMDBp0196893	Myotubularin-related protein 7	Unknown	Q9Y216

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000192	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	VMH	30371894
MMDBr0002304	Uridine diphosphate-N-acetylglucosamine	N-Acetylmannosamine	glucosamine (UDP-N-acetyl)-2-epimerase/N-acetylmannosamine kinase	VMH	10330343 10431835
MMDBr0002457	Uridine diphosphate-N-acetylglucosamine	N-Acetylmannosamine	glucosamine (UDP-N-acetyl)-2-epimerase/N-acetylmannosamine kinase	VMH; KEGG	30371894
MMDBr0006894	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	VMH; KEGG	30371894
MMDBr0006981	Uridine diphosphate-N-acetylglucosamine	N-Acetylmannosamine	Not Available	VMH; KEGG	30371894
MMDBr0007718	N-Acetylmannosamine	N-Acetyl-D-mannosamine 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0008066	N-Acetyl-D-glucosamine	N-Acetylmannosamine	Not Available	VMH; KEGG	30371894
MMDBr0008119	N-Acetylmannosamine	N-Acetylneuraminic acid	Not Available	VMH	30371894

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	Firmicutes	350	Human feces; Human ; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	146	Human feces; Human sputum; Human ; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	85	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	121	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human supragingival plaque; Human subgingival plaque; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	16	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	22944170
Human Feces	Detected but not Quantified	Not Specified	Not Specified	Cryptosporidium infection	HMDB	22944170
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	28157703
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	22944170
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	28157703
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0001129

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028419

KNApSAcK ID

Not Available

Chemspider ID

9271300

KEGG Compound ID

C00645

BioCyc ID

N-ACETYL-D-MANNOSAMINE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

63154

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kamerling JP, Strecker G, Farriaux JP, Dorland L, Haverkamp J, Vliegenthart JF: 2-Acetamidoglucal, a new metabolite isolated from the urine of a patient with sialuria. Biochim Biophys Acta. 1979 Mar 22;583(3):403-8. doi: 10.1016/0304-4165(79)90465-3. [PubMed:444571 ]
Sugawara T, Irie K, Iwasawa H, Yoshikawa T, Okuno S, Watanabe HK, Kato T, Shibukawa M, Ito Y: Synthesis of omega-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates. Carbohydr Res. 1992 Jun 4;230(1):117-49. doi: 10.1016/s0008-6215(00)90517-2. [PubMed:1511450 ]
von Nicolai H, Esser P, Lauer E: Partial purification and properties of neuraminidase from Bifidobacterium lactentis. Hoppe Seylers Z Physiol Chem. 1981 Feb;362(2):153-62. doi: 10.1515/bchm2.1981.362.1.153. [PubMed:7216169 ]
Rodriguez-Aparicio LB, Ferrero MA, Reglero A: N-acetyl-D-neuraminic acid synthesis in Escherichia coli K1 occurs through condensation of N-acetyl-D-mannosamine and pyruvate. Biochem J. 1995 Jun 1;308 ( Pt 2):501-5. doi: 10.1042/bj3080501. [PubMed:7772033 ]
Sala G, Dupre T, Seta N, Codogno P, Ghidoni R: Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts. Pediatr Res. 2002 Nov;52(5):645-51. doi: 10.1203/00006450-200211000-00007. [PubMed:12409508 ]
Salama I, Hinderlich S, Shlomai Z, Eisenberg I, Krause S, Yarema K, Argov Z, Lochmuller H, Reutter W, Dabby R, Sadeh M, Ben-Bassat H, Mitrani-Rosenbaum S: No overall hyposialylation in hereditary inclusion body myopathy myoblasts carrying the homozygous M712T GNE mutation. Biochem Biophys Res Commun. 2005 Mar 4;328(1):221-6. doi: 10.1016/j.bbrc.2004.12.157. [PubMed:15670773 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Showing metabocard for N-Acetylmannosamine (MMDBc0000181)

MOL for #<Metabolite:0x00007fecd8999130>

3D MOL for #<Metabolite:0x00007fecd8999130>

3D SDF for #<Metabolite:0x00007fecd8999130>

3D-SDF for #<Metabolite:0x00007fecd8999130>

PDB for #<Metabolite:0x00007fecd8999130>

3D PDB for #<Metabolite:0x00007fecd8999130>

SMILES for #<Metabolite:0x00007fecd8999130>

INCHI for #<Metabolite:0x00007fecd8999130>

Structure for #<Metabolite:0x00007fecd8999130>

3D Structure for #<Metabolite:0x00007fecd8999130>