NP-MRD: Showing NP-Card for N-Acetylmannosamine (NP0000346)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:38:41 UTC

NP-MRD ID

NP0000346

Secondary Accession Numbers

None

Natural Product 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>
NP0000346

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

Value	Source
beta-ManNAc	ChEBI
N-Acetyl-beta-mannosamine	ChEBI
WURCS=2.0/1,1,0/[a1122h-1b_1-5_2*ncc/3=o]/1/	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 Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-08-10	View Spectrum

Species

Species of Origin

Animalia

Eubacteria

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 )

Physical Properties

State

Solid

Experimental 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	Not Available

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

External Links

HMDB ID

HMDB0001129

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB112379

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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for N-Acetylmannosamine (NP0000346)

MOL for NP0000346 (N-Acetylmannosamine)

3D MOL for NP0000346 (N-Acetylmannosamine)

3D SDF for NP0000346 (N-Acetylmannosamine)

3D-SDF for NP0000346 (N-Acetylmannosamine)

PDB for NP0000346 (N-Acetylmannosamine)

3D PDB for NP0000346 (N-Acetylmannosamine)

SMILES for NP0000346 (N-Acetylmannosamine)

INCHI for NP0000346 (N-Acetylmannosamine)

Structure for NP0000346 (N-Acetylmannosamine)

3D Structure for NP0000346 (N-Acetylmannosamine)