ECMDB: N-acetylneuraminate (ECMDB23218) (M2MDB003608)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (252)

Record Information

Version

2.0

Creation Date

2012-10-10 12:22:33 -0600

Update Date

2015-08-05 16:22:04 -0600

Secondary Accession Numbers

ECMDB23218

Identification

Name:

N-acetylneuraminate

Description

A ketoaldonate that is the conjugate base of N-acetylneuraminic acid, obtained by deprotonation of the carboxy group

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonate
5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid
5-acetamido-3,5-Dideoxy-D-glycero-D-galacto-non-2-ulopyranosonate
5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid
N-acetylneuraminic acid
N-Acetylneuraminic acid
n-Acetylneuraminic acid
NANA
Neu5Ac
NeuNAc
O-Sialate
O-sialic acid
Sialate
Sialic acid

Chemical Formula:

C₁₁H₁₉NO₉

Weight:

Average: 309.2699
Monoisotopic: 309.105981211

InChI Key:

SQVRNKJHWKZAKO-LUWBGTNYSA-N

InChI:

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

CAS number:

131-48-6

IUPAC Name:

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

Traditional IUPAC Name:

NeuAc

SMILES:

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

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 acids (CHEBI:17012 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

186 C

Experimental Properties:

Property	Value	Source

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)	-0.38	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	28.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid
N-acetylneuraminate > N-Acetylmannosamine + Pyruvic acid

SMPDB Pathways:

Not Available

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1092000000-ca2f76604846382a3032	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-6190000000-7e304e9fa3125067d352	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9240000000-65d03a6c6f60a71416c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-074j-4961000000-bc80694ae9687db9a365	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9210000000-c1d9f41a64bc464147dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-a1d857dc5ad7118647b3	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	45744
HMDB ID	HMDB00230
Pubchem Compound ID	445063
Kegg ID	C00270
ChemSpider ID	Not Available
Wikipedia	N-Acetylneuraminic acid
BioCyc ID	N-ACETYLNEURAMINATE
EcoCyc ID	N-ACETYLNEURAMINATE
Ligand Expo	SI2

Enzymes

Protein Details

1. N-acetylneuraminate lyase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate
Gene Name:: nanA
Uniprot ID:: P0A6L4
Molecular weight:: 32593

Reactions

N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate.

N-acetylneuraminate (ECMDB23218) (M2MDB003608)

Structure for #<Compound:0xac06bc04>

Enzymes

Reactions