Showing Compound 2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose (FDB023773)

Record Information

Version

1.0

Creation date

2011-09-21 00:34:31 UTC

Update date

2015-07-21 06:57:51 UTC

Primary ID

FDB023773

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose

Description

2-Acetamido-2-deoxy-6-O-a-L-fucopyranosyl-D-glucose is an oligosaccharide isolated from the urine of patients with fucosidosis (Fucosidosis is an autosomal recessive lysosomal storage disease caused by defective alpha-L-fucosidase with accumulation of fucose in the tissues. Different phenotypes include clinical features such as neurologic deterioration, growth retardation, visceromegaly, and seizures in a severe early form; coarse facial features, angiokeratoma corporis diffusum, spasticity and delayed psychomotor development in a longer surviving form; and an unusual spondylometaphyseoepiphyseal dysplasia in yet another form. OMIM 230000). (PMID 728478) [HMDB]

CAS Number

37776-59-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-a-L-galactopyranosyl)-D-glucose	HMDB
2-(Acetylamino)-2-deoxy-6-O-(6-deoxy-a-L-galactopyranosyl)-D-glucose	hmdb
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-alpha-L-galactopyranosyl)-D-glucose	HMDB
2-(Acetylamino)-2-deoxy-6-O-(6-deoxy-alpha-L-galactopyranosyl)-D-glucose	hmdb
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-alpha-L-galactopyranosyl)-delta-glucose	HMDB
2-Acetamido-2-deoxy-6-O-a-L-fucopyranosyl-D-glucose	Generator
2-Acetamido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucose	Generator
N-{3,4,5-trihydroxy-1-oxo-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl}ethanimidate	Generator, HMDB

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	102 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.6	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	79.32 m³·mol⁻¹	ChemAxon
Polarizability	35.24 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

C14H25NO10

IUPAC name

N-{3,4,5-trihydroxy-1-oxo-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl}acetamide

InChI Identifier

InChI=1S/C14H25NO10/c1-5-9(19)12(22)13(23)14(25-5)24-4-8(18)11(21)10(20)7(3-16)15-6(2)17/h3,5,7-14,18-23H,4H2,1-2H3,(H,15,17)

InChI Key

YBWAUUBLHOFOPK-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OCC(O)C(O)C(O)C(NC(C)=O)C=O)C(O)C(O)C1O

Average Molecular Weight

367.349

Monoisotopic Molecular Weight

367.147846025

Classification

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Amino saccharide
Beta-hydroxy aldehyde
Monosaccharide
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aldehyde
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

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	2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0lxt-8977000000-a2bb860c76008c8ba468	Spectrum
Predicted GC-MS	2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-4236119000-157bdb7a4e39cf80488e	Spectrum
Predicted GC-MS	2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose, non-derivatized, 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	splash10-0uxr-1219000000-f15747e1b5ccf9e81e65	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9720000000-19137fd08ea152aadd6d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-8900000000-f71c7291db908ebd248e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0cea-1923000000-caffbe52ec84c868cb4d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-4921000000-71facf6e0f221fb8e3d4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9710000000-c1d713140c972dfce842	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0229000000-899d186fea014b0d7629	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kh9-9411000000-2a9b99c9e48ef6125eb2	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ac0-9320000000-466625b9719e971e162a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9315000000-e449249c04bae5502537	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-494e7c53dfe677c9151e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-e1289f85de752e1143d5	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

17216351

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

22833656

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05817

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 2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose (FDB023773)

Structure for FDB023773 (2-Acetamido-2-deoxy-6-O-alpha-L-fucopyranosyl-D-glucose)