ContaminantDB: N-Acetyl-alpha-neuraminic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:21:57 UTC

Update Date

2016-11-09 01:21:13 UTC

Accession Number

CHEM034955

Identification

Common Name

N-Acetyl-alpha-neuraminic acid

Class

Small Molecule

Description

N-Acetylneuraminic acid with alpha configuration at the anomeric centre.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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

Chemical Formula

C₁₁H₁₉NO₉

Average Molecular Mass

309.270 g/mol

Monoisotopic Mass

309.106 g/mol

CAS Registry Number

21646-00-4

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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