Showing Compound N-Acetyl-4-O-acetylneuraminic acid (FDB022250)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:53 UTC

Update date

2015-07-21 06:57:05 UTC

Primary ID

FDB022250

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetyl-4-O-acetylneuraminic acid

Description

N-Acetyl-4-O-acetylneuraminic acid, also known as N,4-O-diacetylneuraminate or neu4,5ac2, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-4-O-acetylneuraminic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-acetyl-4-O-acetylneuraminic acid a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on N-Acetyl-4-O-acetylneuraminic acid.

CAS Number

16655-75-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate	HMDB
4-acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonate	hmdb
4-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid	HMDB
4-acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonic acid	hmdb
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate	HMDB
4-acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonate	hmdb
4-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid	HMDB
4-acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-Nonulosonic acid	hmdb
4-O-Acetyl-N-acetylneuraminate	HMDB
4-O-Acetyl-N-acetylneuraminic acid	HMDB

Showing 1 to 10 of 16 entries

Predicted Properties

Property	Value	Source
Water Solubility	135 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-0.42	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	182.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.93 m³·mol⁻¹	ChemAxon
Polarizability	31.77 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

Chemical Formula

C13H21NO10

IUPAC name

(2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C13H21NO10/c1-5(16)14-9-8(23-6(2)17)3-13(22,12(20)21)24-11(9)10(19)7(18)4-15/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7?,8-,9+,10?,11+,13-/m0/s1

InChI Key

LVBIMVQYUKOENY-FODKYPIKSA-N

Isomeric SMILES

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

Average Molecular Weight

351.3065

Monoisotopic Molecular Weight

351.116545897

Classification

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide sulfate
Monosaccharide
Oxane
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Acetamide
1,2-diol
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine sulfate (CHEBI:28132 )
amino monosaccharide (CHEBI:28132 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ec-9023000000-ceae40b20fb24704fc1b	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6270269000-05962272f17756472132	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-4-O-acetylneuraminic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gwf-1049000000-ff6c316b159ea09aabc4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9052000000-31a89bc21243d9ec7aa9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9350000000-e80c07c98be4c8786447	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kac-3197000000-301a2e7803d04e959a18	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9580000000-a3cb7efe371d706a6269	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-e088bc9bb343d1437456	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pvu-7069000000-28cea8c0f9552dc306c1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9030000000-8dfb7a3845c79d40d05a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9240000000-f4f783c555d752999f37	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ul0-0049000000-71afb2af5f35ae6811c4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w30-0197000000-3514308aca46ccb2f36a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qc-6590000000-cd292115e7558d04f9a1	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

389185

ChEMBL ID

Not Available

KEGG Compound ID

C04015

Pubchem Compound ID

440197

Pubchem Substance ID

Not Available

ChEBI ID

32844

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00796

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound N-Acetyl-4-O-acetylneuraminic acid (FDB022250)

Structure for FDB022250 (N-Acetyl-4-O-acetylneuraminic acid)