NP-MRD: Showing NP-Card for N-Acetyl-alpha-neuraminic acid (NP0334660)

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Record Information

Version

2.0

Created at

2024-09-10 19:21:27 UTC

Updated at

2024-09-10 19:21:28 UTC

NP-MRD ID

NP0334660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-alpha-neuraminic acid

Description

N-Acetyl-alpha-neuraminic acid is also known as N-acetyl-a-neuraminate. Based on a literature review very few articles have been published on N-Acetyl-alpha-neuraminic acid.

Structure

MOL SDF PDB SMILES InChI

N-Acetyl-a-neuraminic acid.mol
  Mrv2104 05252321532D          

 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>
NP0334660

> <DATABASE_NAME>
NP-MRD

> <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=1/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+/s2

> <INCHI_KEY>
SQVRNKJHWKZAKO-SYIBJXSDNA-N

> <FORMULA>
C11H19NO9

> <MOLECULAR_WEIGHT>
309.271

> <EXACT_MASS>
309.105981196

> <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

> <JCHEM_LOGP>
-3.5639375190000004

> <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

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylneuraminic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Acetyl-a-neuraminic acid.mol                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         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

View in JSmol

Synonyms

Value	Source
N-Acetyl-a-neuraminate	Generator
N-Acetyl-a-neuraminic acid	Generator
N-Acetyl-alpha-neuraminate	Generator
N-Acetyl-α-neuraminate	Generator
N-Acetyl-α-neuraminic acid	Generator

Chemical Formula

C₁₁H₁₉NO₉

Average Mass

309.2710 Da

Monoisotopic Mass

309.10598 Da

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

Not Available

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=1/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+/s2

InChI Key

SQVRNKJHWKZAKO-SYIBJXSDNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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 )

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	-3.6	ChemAxon
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

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

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for N-Acetyl-alpha-neuraminic acid (NP0334660)

MOL for NP0334660 (N-Acetyl-alpha-neuraminic acid)

3D MOL for NP0334660 (N-Acetyl-alpha-neuraminic acid)

3D SDF for NP0334660 (N-Acetyl-alpha-neuraminic acid)

3D-SDF for NP0334660 (N-Acetyl-alpha-neuraminic acid)

PDB for NP0334660 (N-Acetyl-alpha-neuraminic acid)

3D PDB for NP0334660 (N-Acetyl-alpha-neuraminic acid)

SMILES for NP0334660 (N-Acetyl-alpha-neuraminic acid)

INCHI for NP0334660 (N-Acetyl-alpha-neuraminic acid)

Structure for NP0334660 (N-Acetyl-alpha-neuraminic acid)

3D Structure for NP0334660 (N-Acetyl-alpha-neuraminic acid)