Bovine Metabolome Database: Showing metabocard for N-Acetyl-a-neuraminic acid (BMDB0000773)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:22 UTC

Update Date

2020-04-22 15:05:15 UTC

BMDB ID

BMDB0000773

Secondary Accession Numbers

BMDB00773

Metabolite Identification

Common Name

N-Acetyl-a-neuraminic acid

Description

N-Acetyl-a-neuraminic acid, also known as alpha-neu5ac or O-sialIC ACID, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetyl-a-neuraminic acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on N-Acetyl-a-neuraminic acid.

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 Weight

309.2699

Monoisotopic Molecular Weight

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

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	-2.8	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	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9370000000-a2a8e1f2580c7bb97655	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0pb9-2390148000-6c04c73ad5de1e54ba0e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_5_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("N-Acetyl-a-neuraminic acid,5TBDMS,#15" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03kc-0095000000-8f7746cc3f652b12033f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-1392000000-3e251c9d2583e71f866a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-7910000000-ba41b78e53cb934a9b19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3039000000-4348eff0515b0da3bc08	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-6290000000-5ac6f13cca0827ab0dd0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-9100000000-ac22477eeca403481eff	View in MoNA

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Baumberger, Franz; Vasella, Andrea. , Synthesis of N-acetylneuraminic acid and N-acetyl-4-epineuraminic acid. Helvetica Chimica Acta (1986), 69(5), 1205-15.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Acetyl-a-neuraminic acid (BMDB0000773)

Structure for BMDB0000773 (N-Acetyl-a-neuraminic acid)