NP-MRD: Showing NP-Card for N-Acetyl-D-mannosamine (NP0002605)

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Record Information

Version

1.0

Created at

2020-11-23 18:25:06 UTC

Updated at

2021-08-12 19:51:38 UTC

NP-MRD ID

NP0002605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-D-mannosamine

Provided By

BMRB

Description

N-acetyl-alpha-D-mannosamine, also known as alpha-D-manac or 2-acetamido-2-deoxy-a-D-mannose, 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. N-Acetyl-D-mannosamine is found in Escherichia coli K1. It was first documented in 2002 (PMID: 12355530). Based on a literature review a small amount of articles have been published on N-acetyl-alpha-D-mannosamine (PMID: 17984079) (PMID: 12670660) (PMID: 15280054) (PMID: 15936003).

Structure

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


     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.7819    0.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -0.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955   -1.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068    0.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197   -0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984    1.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977    2.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311    1.8352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8136   -0.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9173   -2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -1.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -2.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3527   -1.2457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    1.5286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1690    0.7122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555    1.4387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6227   -1.3513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    1.5411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903    3.7835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424    2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153   -0.5151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973    1.6407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0016    0.5987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -0.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045   -2.6983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9843   -2.4241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001   -3.4978    0.0000 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  1
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  6
  7 22  1  0
  9 23  1  1
 10 24  1  1
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 14 29  1  1
 15 30  1  0
M  END

NP0002605
     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2720   -0.0690    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2238    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    0.8060   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -0.0767    0.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.1816    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2166    1.1141    0.9956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2424    2.4061    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    0.7066    1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    0.3943   -0.2138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4751    0.4311   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9760   -0.4984    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.0137   -0.4848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6408   -1.2756   -1.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -1.1538   -0.0585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -1.8957    1.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -1.0007    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0902   -0.2391    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.7224    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    1.7949   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    0.6405   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    1.1870    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288    2.3745   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    1.1082   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.4406    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    0.1711   -1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.3290    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770   -1.7128    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.2424   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.7063   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.4899    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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
  3 19  1  0
  5 20  1  6
  6 21  1  1
  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


     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.7819    0.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -0.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1955   -1.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068    0.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8197   -0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4984    1.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977    2.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311    1.8352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8136   -0.3172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9173   -2.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -1.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -2.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3527   -1.2457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111    1.5286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1690    0.7122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555    1.4387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6227   -1.3513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    1.5411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903    3.7835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424    2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153   -0.5151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9973    1.6407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0016    0.5987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046   -0.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045   -2.6983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9843   -2.4241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001   -3.4978    0.0000 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  1
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  1
  6 21  1  6
  7 22  1  0
  9 23  1  1
 10 24  1  1
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 14 29  1  1
 15 30  1  0
M  END
> <DATABASE_ID>
NP0002605

> <DATABASE_NAME>
NP-MRD

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

> <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-UOLFYFMNSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
20.69965054645778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.31

> <JCHEM_LOGP>
-2.400970284666667

> <ALOGPS_LOGS>
-0.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.712808212369529

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3833249460656685

> <JCHEM_PKA_STRONGEST_BASIC>
1.4626404621026499

> <JCHEM_POLAR_SURFACE_AREA>
122.74000000000002

> <JCHEM_REFRACTIVITY>
47.5464

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.25e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002605
     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.2720   -0.0690    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2238    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    0.8060   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -0.0767    0.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.1816    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2166    1.1141    0.9956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2424    2.4061    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    0.7066    1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    0.3943   -0.2138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4751    0.4311   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9760   -0.4984    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.0137   -0.4848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6408   -1.2756   -1.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -1.1538   -0.0585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -1.8957    1.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -1.0007    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0902   -0.2391    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.7224    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    1.7949   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    0.6405   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    1.1870    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288    2.3745   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    1.1082   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.4406    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    0.1711   -1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.3290    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770   -1.7128    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.2424   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.7063   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.4899    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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
  3 19  1  0
  5 20  1  6
  6 21  1  1
  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                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4   10                                                       
CONECT    3    1    9   11                                                  
CONECT    4    2    6   15   16                                             
CONECT    5    7    8    9   17                                             
CONECT    6    4    7   12   18                                             
CONECT    7    5    6   13   19                                             
CONECT    8    5   14   15   20                                             
CONECT    9    3    5                                                       
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    4    8                                                       
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    NP0002605
HETATM    1  C1  UNL     1       4.272  -0.069   0.882  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.978   0.224   0.179  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.976   0.806  -1.081  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.889  -0.077   0.771  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.615   0.182   0.144  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.217   1.114   0.996  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.242   2.406   0.439  1.00  0.00           O  
HETATM    8  O3  UNL     1      -1.543   0.707   1.094  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.955   0.394  -0.214  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.475   0.431  -0.232  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.976  -0.498   0.667  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.504  -1.014  -0.485  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.641  -1.276  -1.841  1.00  0.00           O  
HETATM   14  C8  UNL     1      -0.071  -1.154  -0.058  1.00  0.00           C  
HETATM   15  O6  UNL     1      -0.029  -1.896   1.118  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.109  -1.001   1.477  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.090  -0.239   0.171  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.505   0.722   1.624  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.111   1.795  -1.225  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.756   0.641  -0.845  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.262   1.187   1.983  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.029   2.375  -0.512  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.534   1.108  -0.929  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.851   1.441   0.028  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.861   0.171  -1.235  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.226  -1.329   0.203  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.177  -1.713   0.061  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.462  -2.242  -2.021  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.523  -1.706  -0.813  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.649  -1.490   1.724  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    4
CONECT    3   19
CONECT    4    5
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

NP0002605
     RDKit          3D

30 30  0  0  0  0  0  0  0  0999 V2000
    4.2720   -0.0690    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2238    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    0.8060   -1.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888   -0.0767    0.7710 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.1816    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2166    1.1141    0.9956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2424    2.4061    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    0.7066    1.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    0.3943   -0.2138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4751    0.4311   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9760   -0.4984    0.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5039   -1.0137   -0.4848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6408   -1.2756   -1.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -1.1538   -0.0585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -1.8957    1.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -1.0007    1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0902   -0.2391    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.7224    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    1.7949   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7564    0.6405   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    1.1870    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288    2.3745   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    1.1082   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    1.4406    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    0.1711   -1.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.3290    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770   -1.7128    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -2.2424   -2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229   -1.7063   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6492   -1.4899    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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
  3 19  1  0
  5 20  1  6
  6 21  1  1
  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
2-(ACETYLAMINO)-2-deoxy-ALPHA-D-mannopyranose	ChEBI
2-Acetamido-2-deoxy-alpha-D-mannose	ChEBI
2-Acetylamino-alpha-D-2-deoxy-mannopyranose	ChEBI
alpha-D-ManAc	ChEBI
alpha-D-ManpAc	ChEBI
alpha-ManAc	ChEBI
WURCS=2.0/1,1,0/[a1122h-1a_1-5_2*ncc/3=o]/1/	ChEBI
2-(ACETYLAMINO)-2-deoxy-a-D-mannopyranose	Generator
2-(ACETYLAMINO)-2-deoxy-α-D-mannopyranose	Generator
2-Acetamido-2-deoxy-a-D-mannose	Generator
2-Acetamido-2-deoxy-α-D-mannose	Generator
2-Acetylamino-a-D-2-deoxy-mannopyranose	Generator
2-Acetylamino-α-D-2-deoxy-mannopyranose	Generator
a-D-ManAc	Generator
Α-D-manac	Generator
a-D-ManpAc	Generator
Α-D-manpac	Generator
a-ManAc	Generator
Α-manac	Generator
N-Acetyl-a-D-mannosamine	Generator
N-Acetyl-α-D-mannosamine	Generator
N-Acetyl-D-mannosamine	MeSH
N-Acetylmannosamine, (L)-isomer	MeSH
N-Acetylmannosamine	MeSH
N-Acetylmannosamine, (D)-isomer	MeSH
2-Acetamido-2-deoxy-D-mannose	MeSH

Chemical Formula

C₈H₁₅NO₆

Average Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

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-UOLFYFMNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Escherichia coli K1	Bacteria	KNApSAcK

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-acetylmannosamine (CHEBI:41112 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-2.4	ChemAxon
logS	-0.43	ALOGPS
pKa (Strongest Acidic)	7.38	ChemAxon
pKa (Strongest Basic)	1.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	20.7 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

559205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

41112

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Berkin A, Coxon B, Pozsgay V: Towards a synthetic glycoconjugate vaccine against Neisseria meningitidis A. Chemistry. 2002 Oct 4;8(19):4424-33. doi: 10.1002/1521-3765(20021004)8:19<4424::AID-CHEM4424>3.0.CO;2-1. [PubMed:12355530 ]
Wada M, Hsu CC, Franke D, Mitchell M, Heine A, Wilson I, Wong CH: Directed evolution of N-acetylneuraminic acid aldolase to catalyze enantiomeric aldol reactions. Bioorg Med Chem. 2003 May 1;11(9):2091-8. doi: 10.1016/s0968-0896(03)00052-x. [PubMed:12670660 ]
Pan Y, Ayani T, Nadas J, Wen S, Guo Z: Accessibility of N-acyl-D-mannosamines to N-acetyl-D-neuraminic acid aldolase. Carbohydr Res. 2004 Aug 23;339(12):2091-100. doi: 10.1016/j.carres.2004.05.028. [PubMed:15280054 ]
Coxon B: Deuterium isotope effects in carbohydrates revisited. Cryoprobe studies of the anomerization and NH to ND deuterium isotope induced 13C NMR chemical shifts of acetamidodeoxy and aminodeoxy sugars. Carbohydr Res. 2005 Jul 25;340(10):1714-21. doi: 10.1016/j.carres.2005.04.022. [PubMed:15936003 ]

Showing NP-Card for N-Acetyl-D-mannosamine (NP0002605)

MOL for NP0002605 (N-Acetyl-D-mannosamine)

3D MOL for NP0002605 (N-Acetyl-D-mannosamine)

3D SDF for NP0002605 (N-Acetyl-D-mannosamine)

3D-SDF for NP0002605 (N-Acetyl-D-mannosamine)

PDB for NP0002605 (N-Acetyl-D-mannosamine)

3D PDB for NP0002605 (N-Acetyl-D-mannosamine)

SMILES for NP0002605 (N-Acetyl-D-mannosamine)

INCHI for NP0002605 (N-Acetyl-D-mannosamine)

Structure for NP0002605 (N-Acetyl-D-mannosamine)

3D Structure for NP0002605 (N-Acetyl-D-mannosamine)