MiMeDB: Showing metabocard for N-Acetyl-alpha-neuraminate (MMDBc0031156)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:37:38 UTC

Update Date

2022-08-31 17:58:57 UTC

Metabolite ID

MMDBc0031156

Metabolite Identification

Common Name

N-Acetyl-alpha-neuraminate

Description

N-Acetyl-alpha-neuraminate is a sialic acid. Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. They can be utilized by pathogens to evade the host immune response. N-acetylneuraminic acid is the most common sialic acid. A number of bacteria that can colonize humans (such as E. coli) make use of N-acetylneuraminic acid as a nutrient source. Production of the enzymes involved in N-acetylneuraminate degradation is induced by growth on sialic acid as the sole source of carbon, which is due to transcriptional regulation by the repressor NanR.‚Üµ

Structure

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

HMDB0000773
     RDKit          3D
N-Acetyl-a-neuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.5392   -4.0642   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -2.7604    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6531   -2.7419    1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366   -1.5662   -0.4907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -0.3089    0.0711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9572    0.5700    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418    0.0140    0.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    1.9190    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233    2.4959   -0.5117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4663    3.2153    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    3.4980   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    3.1424   -1.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    4.8517   -1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1693    1.5428   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    0.3861   -0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6508    0.5886   -0.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5928    1.0142   -1.0675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.7111    0.4321 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4563   -0.4840    1.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -1.7159   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306   -2.8566   -0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -4.5617   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -3.9305   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -4.7161    0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952   -1.5615   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.5031    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071    0.6387   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328    0.2215    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282    1.8265    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3680    2.5561    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050    3.4841   -0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7648    5.4527   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189   -0.3086   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287    1.3070    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    0.8321   -1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819   -1.1577    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845    0.4251    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581   -1.9908   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -1.2573   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -2.7853   -0.1125 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  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  6
 16 34  1  1
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

N-Acetyl-a-neuraminic acid.mol
  Mrv1652305231920062D          

 22 22  0  0  0  0            999 V2000
   -1.4531    0.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -0.0848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7387   -0.4973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0242   -0.0848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0225    0.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7387    1.1527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7885    0.0573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0717    0.8322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8844    0.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676    1.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692    1.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    1.7850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    1.6409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873    2.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -0.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7387   -1.3223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575   -0.8603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423    1.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -2.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -1.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -1.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
  6 11  1  6  0  0  0
  6 12  1  1  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
  2 15  1  1  0  0  0
  7 16  1  1  0  0  0
  3 17  1  6  0  0  0
  4 18  1  6  0  0  0
  8 19  1  6  0  0  0
 17 21  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031156

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1

> <INCHI_KEY>
SQVRNKJHWKZAKO-YRMXFSIDSA-N

> <FORMULA>
C11H19NO9

> <MOLECULAR_WEIGHT>
309.2699

> <EXACT_MASS>
309.105981211

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.19107319495126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-3.5639375190000004

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.10700253474434

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9966581465692994

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3430861642982177

> <JCHEM_POLAR_SURFACE_AREA>
176.77999999999997

> <JCHEM_REFRACTIVITY>
63.7814

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylneuraminic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000773
     RDKit          3D
N-Acetyl-a-neuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.5392   -4.0642   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -2.7604    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6531   -2.7419    1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366   -1.5662   -0.4907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -0.3089    0.0711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9572    0.5700    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418    0.0140    0.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    1.9190    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233    2.4959   -0.5117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4663    3.2153    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    3.4980   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    3.1424   -1.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    4.8517   -1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1693    1.5428   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    0.3861   -0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6508    0.5886   -0.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5928    1.0142   -1.0675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.7111    0.4321 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4563   -0.4840    1.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -1.7159   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306   -2.8566   -0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -4.5617   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -3.9305   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -4.7161    0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952   -1.5615   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.5031    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071    0.6387   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328    0.2215    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282    1.8265    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3680    2.5561    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050    3.4841   -0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7648    5.4527   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189   -0.3086   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287    1.3070    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    0.8321   -1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819   -1.1577    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845    0.4251    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581   -1.9908   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -1.2573   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -2.7853   -0.1125 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  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  6
 16 34  1  1
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Acetyl-a-neuraminic acid.mol                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.712   1.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.712  -0.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.379  -0.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.045  -0.158   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.042   1.382   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.379   2.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.472   0.107   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001   1.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.518   1.819   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.046   3.265   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.369   3.331   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.390   3.332   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.886   3.063   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.843   4.778   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.046  -0.928   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.460  -1.074   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -1.379  -2.468   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0       0.481  -1.606   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0       1.012   2.734   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.712  -4.778   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.712  -3.238   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.046  -2.468   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5    7   18                                             
CONECT    5    4    6                                                       
CONECT    6    5    1   11   12                                             
CONECT    7    4    8   16                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   13   14                                                  
CONECT   12    6                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    2                                                            
CONECT   16    7                                                            
CONECT   17    3   21                                                       
CONECT   18    4                                                            
CONECT   19    8                                                            
CONECT   20   21                                                            
CONECT   21   17   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0000773
HETATM    1  C1  UNL     1      -1.539  -4.064  -0.324  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.091  -2.760   0.235  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.653  -2.742   1.413  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.137  -1.566  -0.491  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.695  -0.309   0.071  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.957   0.570   0.121  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.942   0.014   0.896  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.486   1.919   0.612  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.623   2.496  -0.512  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.466   3.215   0.022  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.480   3.498  -1.205  1.00  0.00           C  
HETATM   12  O4  UNL     1      -2.539   3.142  -1.784  1.00  0.00           O  
HETATM   13  O5  UNL     1      -1.176   4.852  -1.257  1.00  0.00           O  
HETATM   14  O6  UNL     1      -0.169   1.543  -1.378  1.00  0.00           O  
HETATM   15  C8  UNL     1       0.310   0.386  -0.793  1.00  0.00           C  
HETATM   16  C9  UNL     1       1.651   0.589  -0.126  1.00  0.00           C  
HETATM   17  O7  UNL     1       2.593   1.014  -1.067  1.00  0.00           O  
HETATM   18  C10 UNL     1       2.194  -0.711   0.432  1.00  0.00           C  
HETATM   19  O8  UNL     1       3.456  -0.484   1.032  1.00  0.00           O  
HETATM   20  C11 UNL     1       2.493  -1.716  -0.690  1.00  0.00           C  
HETATM   21  O9  UNL     1       3.031  -2.857  -0.083  1.00  0.00           O  
HETATM   22  H1  UNL     1      -0.693  -4.562  -0.854  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.377  -3.931  -1.046  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.873  -4.716   0.498  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.495  -1.562  -1.465  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.335  -0.503   1.111  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.307   0.639  -0.923  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.833   0.221   0.469  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.928   1.826   1.556  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.368   2.556   0.821  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.005   3.484  -0.762  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.765   5.453  -0.659  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.519  -0.309  -1.662  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.629   1.307   0.702  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.235   0.832  -1.959  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.582  -1.158   1.220  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.485   0.425   1.455  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.558  -1.991  -1.196  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.249  -1.257  -1.357  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.007  -2.785  -0.113  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5   25
CONECT    5    6   15   26
CONECT    6    7    8   27
CONECT    7   28
CONECT    8    9   29   30
CONECT    9   10   11   14
CONECT   10   31
CONECT   11   12   12   13
CONECT   13   32
CONECT   14   15
CONECT   15   16   33
CONECT   16   17   18   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   38   39
CONECT   21   40
END

HMDB0000773
     RDKit          3D
N-Acetyl-a-neuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.5392   -4.0642   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907   -2.7604    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6531   -2.7419    1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366   -1.5662   -0.4907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -0.3089    0.0711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9572    0.5700    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9418    0.0140    0.8957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    1.9190    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233    2.4959   -0.5117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4663    3.2153    0.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    3.4980   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    3.1424   -1.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    4.8517   -1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1693    1.5428   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    0.3861   -0.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6508    0.5886   -0.1257 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5928    1.0142   -1.0675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.7111    0.4321 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4563   -0.4840    1.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -1.7159   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306   -2.8566   -0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -4.5617   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -3.9305   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8734   -4.7161    0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952   -1.5615   -1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.5031    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071    0.6387   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328    0.2215    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282    1.8265    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3680    2.5561    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050    3.4841   -0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7648    5.4527   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189   -0.3086   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287    1.3070    0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348    0.8321   -1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819   -1.1577    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845    0.4251    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581   -1.9908   -1.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487   -1.2573   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071   -2.7853   -0.1125 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  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  6
 16 34  1  1
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

Synonyms

Value	Source
alpha-Neu5ac	ChEBI
O-SIALIC ACID	ChEBI
WURCS=2.0/1,1,0/[aad21122h-2a_2-6_5*ncc/3=o]/1/	ChEBI
a-Neu5ac	Generator
Α-neu5ac	Generator
O-SIALate	Generator
N-Acetyl-a-neuraminate	Generator
5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonic acid	HMDB
5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonate	HMDB
5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonic acid	HMDB
5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonate	HMDB
5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonic acid	HMDB
N-Acetyl-a-D-neuraminate	HMDB
N-Acetyl-a-D-neuraminic acid	HMDB
N-Acetyl-alpha-delta-neuraminate	HMDB
N-Acetyl-alpha-delta-neuraminic acid	HMDB
N-Acetyl-alpha-neuraminate	HMDB
PolySia	HMDB
Polysialic acid	HMDB
N-Acetyl-alpha-neuraminic acid	HMDB
N-Acetyl-α-neuraminate	HMDB
N-Acetyl-α-neuraminic acid	HMDB
Acid, N-acetylneuraminic	HMDB
Acid, sialic	HMDB
N Acetylneuraminic acid	HMDB
N-Acetylneuraminic acid	HMDB
Sialic acid	HMDB
N-Acetyl-a-neuraminic acid	Generator

Molecular Formula

C₁₁H₁₉NO₉

Average Mass

309.2699

Monoisotopic Mass

309.105981211

IUPAC Name

(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

N-acetylneuraminic acid

CAS Registry Number

21646-00-4

SMILES

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

InChI Identifier

InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1

InChI Key

SQVRNKJHWKZAKO-YRMXFSIDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

N-acylneuraminic acid
Neuraminic acid
C-glucuronide
C-glycosyl compound
Glycosyl compound
Alpha-hydroxy acid
Pyran
Hydroxy acid
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Organic oxide
Carbonyl group
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetylneuraminic acid (CHEBI:49026 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	227 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.6	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	176.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.78 m³·mol⁻¹	ChemAxon
Polarizability	28.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9370000000-a2a8e1f2580c7bb97655	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0pb9-2390148000-6c04c73ad5de1e54ba0e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_5_15) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("N-Acetyl-a-neuraminic acid,5TBDMS,#15" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1092000000-ca2f76604846382a3032	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-6190000000-7e304e9fa3125067d352	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9240000000-65d03a6c6f60a71416c6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-074j-4961000000-bc80694ae9687db9a365	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9210000000-c1d9f41a64bc464147dd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-a1d857dc5ad7118647b3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03kc-0095000000-8f7746cc3f652b12033f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-1392000000-3e251c9d2583e71f866a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-7910000000-ba41b78e53cb934a9b19	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3039000000-4348eff0515b0da3bc08	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-6290000000-5ac6f13cca0827ab0dd0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-9100000000-ac22477eeca403481eff	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014525	N-Acetyl-alpha-neuraminate	N-acetyl-beta-neuraminic acid	N-acetylneuraminate epimerase	Epimerization	RHEA	34755880
MMDBr0014526	N-Acetyl-alpha-neuraminate	N-acetyl-beta-neuraminic acid	N-acetylneuraminate epimerase	Epimerization	RHEA	34755880
MMDBr0014527	N-acetyl-beta-neuraminic acid	N-Acetyl-alpha-neuraminate	N-acetylneuraminate epimerase	Epimerization	RHEA	34755880
MMDBr0017682	N-Acetyl-alpha-neuraminate	N-acetylneuraminate	N-acetylneuraminate anomerase NanQ	Formation of anomers	RHEA	34755880
MMDBr0017683	N-Acetyl-alpha-neuraminate	N-acetylneuraminate	N-acetylneuraminate anomerase NanQ	Formation of anomers	RHEA	34755880
MMDBr0017684	N-acetylneuraminate	N-Acetyl-alpha-neuraminate	N-acetylneuraminate anomerase NanQ	Formation of anomers	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	40	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Sheep ; Chicken	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0000773

DrugBank ID

DB03721

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022234

KNApSAcK ID

Not Available

Chemspider ID

392681

KEGG Compound ID

C19909

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5739

PubChem Compound

444885

PDB ID

Not Available

ChEBI ID

49026

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]

Showing metabocard for N-Acetyl-alpha-neuraminate (MMDBc0031156)

MOL for #<Metabolite:0x000055c79c2d4ce0>

3D MOL for #<Metabolite:0x000055c79c2d4ce0>

3D SDF for #<Metabolite:0x000055c79c2d4ce0>

3D-SDF for #<Metabolite:0x000055c79c2d4ce0>

PDB for #<Metabolite:0x000055c79c2d4ce0>

3D PDB for #<Metabolite:0x000055c79c2d4ce0>

SMILES for #<Metabolite:0x000055c79c2d4ce0>

INCHI for #<Metabolite:0x000055c79c2d4ce0>

Structure for #<Metabolite:0x000055c79c2d4ce0>

3D Structure for #<Metabolite:0x000055c79c2d4ce0>