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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001129

Secondary Accession Numbers

HMDB0062724
HMDB01129
HMDB62724

Metabolite Identification

Common Name

N-Acetylmannosamine

Description

N-Acetylmannosamine, also known as beta-ManNAcc or β-ManNAc, 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. Within humans, N-acetylmannosamine participates in a number of enzymatic reactions. In particular, N-acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine, which is catalyzed by the enzyme N-acylglucosamine 2-epimerase. In addition, N-acetylmannosamine and uridine 5'-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In humans, N-acetylmannosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. In the rate-limiting step of the pathway, UDP-GlcNAc is converted into ManNAc by UDP-GlcNAc 2-epimerase, encoded by the epimerase domain of GNE. Improved sialylation after the addition of ManNAc and other supporting ingredients to the culture medium not only increases manufacturing yield, but also improves therapeutic efficacy by increasing solubility, increasing half-life and reducing immunogenicity by reducing the formation of antibodies to the therapeutic glycoprotein When the GNE epimerase kinase does not function correctly in the human body thereby reducing the available ManNAc, it is reasonable to assume that treatment with ManNAc could assist with improving health benefits. There is no available therapy to treat GNE myopathy. ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid).

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>
HMDB0001129

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

Fibroblasts (HMDB: HMDB0001129)

Tissue

Muscle tissue

Skeletal Muscle (HMDB: HMDB0001129)

Organ

Prostate (HMDB: HMDB0001129)

Biofluid or Excreta

Excreta

Feces (PMID: 22411374)
Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0001129)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (PathBank: SMP0000045)
N-Acetylneuraminate, N-Acetylmannosamine, and N-Acetylglucosamine Degradation (PathBank: SMP0002044)

Disease pathway

Sialuria or French Type Sialuria (PathBank: SMP0000216)
Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0000240)
Tay-Sachs Disease (PathBank: SMP0000390)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.22	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.591	31661259
DarkChem	[M-H]-	144.74	31661259
AllCCS	[M+H]+	149.735	32859911
AllCCS	[M-H]-	145.931	32859911
DeepCCS	[M+H]+	151.09	30932474
DeepCCS	[M-H]-	148.694	30932474
DeepCCS	[M-2H]-	183.069	30932474
DeepCCS	[M+Na]+	157.602	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.4	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylmannosamine	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	3657.7	Standard polar	33892256
N-Acetylmannosamine	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2082.8	Standard non polar	33892256
N-Acetylmannosamine	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O	2104.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylmannosamine,1TMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	1894.9	Semi standard non polar	33892256
N-Acetylmannosamine,1TMS,isomer #2	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1900.1	Semi standard non polar	33892256
N-Acetylmannosamine,1TMS,isomer #3	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1898.0	Semi standard non polar	33892256
N-Acetylmannosamine,1TMS,isomer #4	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1908.2	Semi standard non polar	33892256
N-Acetylmannosamine,1TMS,isomer #5	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1835.0	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	1915.8	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #10	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1897.1	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #2	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1930.3	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #3	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1938.6	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #4	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1890.6	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #5	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1939.6	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #6	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1939.6	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #7	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1911.9	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #8	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1933.2	Semi standard non polar	33892256
N-Acetylmannosamine,2TMS,isomer #9	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1895.9	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2003.5	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #10	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1967.8	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #2	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2011.5	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #3	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C	1939.5	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #4	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2016.7	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #5	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1961.8	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #6	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1981.0	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #7	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2006.4	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #8	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	1967.9	Semi standard non polar	33892256
N-Acetylmannosamine,3TMS,isomer #9	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	1970.5	Semi standard non polar	33892256
N-Acetylmannosamine,4TMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2036.2	Semi standard non polar	33892256
N-Acetylmannosamine,4TMS,isomer #2	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C	2024.8	Semi standard non polar	33892256
N-Acetylmannosamine,4TMS,isomer #3	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2040.9	Semi standard non polar	33892256
N-Acetylmannosamine,4TMS,isomer #4	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2039.6	Semi standard non polar	33892256
N-Acetylmannosamine,4TMS,isomer #5	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2031.3	Semi standard non polar	33892256
N-Acetylmannosamine,5TMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2092.3	Semi standard non polar	33892256
N-Acetylmannosamine,5TMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2154.1	Standard non polar	33892256
N-Acetylmannosamine,5TMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C	2100.6	Standard polar	33892256
N-Acetylmannosamine,1TBDMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	2151.2	Semi standard non polar	33892256
N-Acetylmannosamine,1TBDMS,isomer #2	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2148.3	Semi standard non polar	33892256
N-Acetylmannosamine,1TBDMS,isomer #3	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2164.7	Semi standard non polar	33892256
N-Acetylmannosamine,1TBDMS,isomer #4	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2166.9	Semi standard non polar	33892256
N-Acetylmannosamine,1TBDMS,isomer #5	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2109.9	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2423.5	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #10	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2384.2	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #2	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2439.8	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #3	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2433.2	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #4	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2371.0	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #5	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2427.0	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #6	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2436.0	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #7	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2406.0	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #8	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2423.5	Semi standard non polar	33892256
N-Acetylmannosamine,2TBDMS,isomer #9	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2389.3	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2686.1	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #10	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2624.3	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #2	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2664.9	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #3	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C	2622.2	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #4	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2659.1	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #5	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2629.1	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #6	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2628.6	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #7	CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2682.8	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #8	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2658.8	Semi standard non polar	33892256
N-Acetylmannosamine,3TBDMS,isomer #9	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2650.9	Semi standard non polar	33892256
N-Acetylmannosamine,4TBDMS,isomer #1	CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2872.7	Semi standard non polar	33892256
N-Acetylmannosamine,4TBDMS,isomer #2	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C	2860.6	Semi standard non polar	33892256
N-Acetylmannosamine,4TBDMS,isomer #3	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.4	Semi standard non polar	33892256
N-Acetylmannosamine,4TBDMS,isomer #4	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2849.9	Semi standard non polar	33892256
N-Acetylmannosamine,4TBDMS,isomer #5	CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2868.3	Semi standard non polar	33892256
N-Acetylmannosamine,5TBDMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.4	Semi standard non polar	33892256
N-Acetylmannosamine,5TBDMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3050.3	Standard non polar	33892256
N-Acetylmannosamine,5TBDMS,isomer #1	CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2705.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetylmannosamine GC-MS (4 TMS)	splash10-00di-1910000000-c54e9f9969c7d963036f	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 5 TMS)	splash10-0pvi-1951000000-56398608d2dd4355e1f6	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 4 TMS)	splash10-0kw0-3940000000-02993315f1b1a700b7ec	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 5 TMS)	splash10-0pvi-2941000000-c2e3ada4d3e27dc6890a	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-7920000000-9991e74281c314048f5e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (4 TMS) - 70eV, Positive	splash10-0007-3331900000-c6fab10d67507eecce65	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004r-0920000000-26c87e12e0c8c5f919b7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9400000000-f0d2f81f4292b627f0ef	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001j-9000000000-fcbf9adb619f826e3cd3	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Positive-QTOF	splash10-00di-0390000000-ce54c5d356ec2fc8ab9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Positive-QTOF	splash10-0il0-2950000000-e4e02ffea74d8dfd0810	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Positive-QTOF	splash10-01ox-9400000000-180503dcc7682bb1753b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Negative-QTOF	splash10-00dr-9830000000-a5028d14de09cabbb303	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Negative-QTOF	splash10-0ac0-9820000000-d3017a9fb13bdc3aa847	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Negative-QTOF	splash10-0a4l-9200000000-ce24407926ce180ba365	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Positive-QTOF	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Positive-QTOF	splash10-0h90-9740000000-db880363194a3979c637	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Positive-QTOF	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Negative-QTOF	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Negative-QTOF	splash10-0abc-9540000000-a1f7d557237a521d306a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Negative-QTOF	splash10-0a4i-9000000000-18eabe9e3d3657888360	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Feces
Urine

Tissue Locations

Fibroblasts
Prostate
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available
Salla Disease/Infantile Sialic Acid Storage Disease		Not Available
Tay-Sachs Disease		Not Available
G(M2)-Gangliosidosis: Variant B, Tay-sachs disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

VMH ID

ACMANA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical & Pharmaceutical Bulletin (1964), 12(5), 615-19.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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. [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. [PubMed:15670773 ]
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. [PubMed:1511450 ]
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. [PubMed:444571 ]
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. [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. [PubMed:7772033 ]

Enzymes

Enzyme Details

1. Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase

General function:: Involved in ATP binding
Specific function:: Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:: GNE
Uniprot ID:: Q9Y223
Molecular weight:: 83065.25

Reactions

Uridine diphosphate-N-acetylglucosamine + Water → N-Acetylmannosamine + Uridine 5'-diphosphate	details
Adenosine triphosphate + N-Acetylmannosamine → ADP + N-Acetyl-D-mannosamine 6-phosphate	details

Enzyme Details

2. Sialic acid synthase

General function:: Involved in catalytic activity
Specific function:: Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:: NANS
Uniprot ID:: Q9NR45
Molecular weight:: 40307.26

Reactions

Phosphoenolpyruvic acid + N-Acetylmannosamine + Water → Phosphate + N-Acetylneuraminic acid	details

Enzyme Details

3. N-acylglucosamine 2-epimerase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion of N-acetylglucosamine to N-acetylmannosamine. Binds to renin forming a protein complex called high molecular weight (HMW) renin and inhibits renin activity. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:: RENBP
Uniprot ID:: P51606
Molecular weight:: 48830.6

Reactions

N-Acetyl-D-glucosamine → N-Acetylmannosamine	details

Enzyme Details

4. N-acetylneuraminate lyase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate. It prevents sialic acids from being recycled and returning to the cell surface. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded (By similarity).
Gene Name:: NPL
Uniprot ID:: Q9BXD5
Molecular weight:: 33116.95

Reactions

N-Acetylneuraminic acid → N-Acetylmannosamine + Pyruvic acid	details

Enzyme Details

5. 14 kDa phosphohistidine phosphatase

General function:: Involved in phosphohistidine phosphatase activity
Specific function:: Exhibits phosphohistidine phosphatase activity.
Gene Name:: PHPT1
Uniprot ID:: Q9NRX4
Molecular weight:: Not Available

Reactions

N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Water	details

Enzyme Details

6. Myotubularin-related protein 1

General function:: Not Available
Specific function:: Lipid phosphatase that acts on phosphatidylinositol 3-phosphate and phosphatidylinositol (3,5)-bisphosphate.
Gene Name:: MTMR1
Uniprot ID:: Q13613
Molecular weight:: Not Available

Reactions

N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Water	details

Enzyme Details

7. Myotubularin-related protein 2

General function:: Not Available
Specific function:: Phosphatase that acts on lipids with a phosphoinositol headgroup. Has phosphatase activity towards phosphatidylinositol 3-phosphate and phosphatidylinositol 3,5-bisphosphate.
Gene Name:: MTMR2
Uniprot ID:: Q13614
Molecular weight:: Not Available

Reactions

N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Water	details

Enzyme Details

8. Myotubularin-related protein 6

General function:: Not Available
Specific function:: Phosphatase that acts on lipids with a phosphoinositol headgroup. Acts as a negative regulator of KCNN4/KCa3.1 channel activity in CD4+ T-cells possibly by decreasing intracellular levels of phosphatidylinositol 3 phosphatase. Negatively regulates proliferation of reactivated CD4+ T-cells.
Gene Name:: MTMR6
Uniprot ID:: Q9Y217
Molecular weight:: Not Available

Reactions

N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Water	details

Enzyme Details

9. Myotubularin-related protein 7

General function:: Not Available
Specific function:: Phosphatase that acts on lipids with a phosphoinositol headgroup (Probable).
Gene Name:: MTMR7
Uniprot ID:: Q9Y216
Molecular weight:: Not Available

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N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Water	details

Showing metabocard for N-Acetylmannosamine (HMDB0001129)

MOL for HMDB0001129 (N-Acetylmannosamine)

3D MOL for HMDB0001129 (N-Acetylmannosamine)

3D SDF for HMDB0001129 (N-Acetylmannosamine)

3D-SDF for HMDB0001129 (N-Acetylmannosamine)

PDB for HMDB0001129 (N-Acetylmannosamine)

3D PDB for HMDB0001129 (N-Acetylmannosamine)

SMILES for HMDB0001129 (N-Acetylmannosamine)

INCHI for HMDB0001129 (N-Acetylmannosamine)

Structure for HMDB0001129 (N-Acetylmannosamine)

3D Structure for HMDB0001129 (N-Acetylmannosamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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