ChemFOnt: Showing chemical card for N-Acetyl-D-glucosamine (CFc000000141)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:27 UTC

Chemfont ID

CFc000000141

Molecule Identification

Common Name

N-Acetyl-D-glucosamine

Definition

N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Acetamido-2-deoxy-D-glucose	ChEBI
GlcNAc	ChEBI
N-Acetylchitosamine	ChEBI
2-(Acetylamino)-2-deoxyhexose	HMDB
2-Acetamido-2-deoxy-D-glucopyranose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
2-Acetamido-D-glucose	HMDB
2-Acetylamino-2-deoxy-D-glucose	HMDB
Acetylglucosamine	HMDB
N-Acetylglucosamine	HMDB
N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide	HMDB
2 Acetamido 2 deoxyglucose	HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

GlcNAc

CAS Registry Number

7512-17-6

SMILES

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

InChI Identifier

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1

InChI Key

OVRNDRQMDRJTHS-RTRLPJTCSA-N

Chemical Taxonomy

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
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetylglucosamine (CHEBI:506227 )
Amino sugars (C00140 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0000215)

Organ

Cell

Neuron (HMDB: HMDB0000215)

Hematocyte

Platelet (HMDB: HMDB0000215)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)
Feces (PMID: 20669995)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000215)

Source

Endogenous

Endogenous (HMDB: HMDB0000215)

Plant

Plant (HMDB: HMDB0000215)

Exogenous

Food

Food (HMDB: HMDB0000215)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Drupe

Peach (FooDB: FOOD00149)

Exogenous (HMDB: HMDB0000215)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (HMDB: HMDB0000215)
Amino Sugar Metabolism (PathBank: SMP0063580)
Amino Sugar and Nucleotide Sugar Metabolism III (PathBank: SMP0121303)
1,6-Anhydro-N-acetylmuramic Acid Recycling (PathBank: SMP0122240)
Inner Membrane Transport (PathBank: SMP0121270)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Amino Sugar and Nucleotide Sugar Metabolism II (PathBank: SMP0000906)

Disease pathway

Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Tay-Sachs Disease (PathBank: SMP0120545)

Role

Industrial application

Food and nutrition

Nutritional supplement (HMDB: HMDB0000215)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	20.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon