Showing Compound N-Acetylglucosamine (FDB008032)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:53 UTC

Update date

2019-11-26 03:01:56 UTC

Primary ID

FDB008032

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetylglucosamine

Description

Monomer of Chitinand is also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD) N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. N-Acetylglucosamine is found in peach.

CAS Number

7512-17-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-(Acetylamino)-2-deoxyglucose, 9CI	manual
2-(Acetylamino)-2-deoxyhexose	HMDB
2-(acetylamino)-2-Deoxyhexose	HMDB
2-Acetamido-2-deoxy-D-glucopyranose	HMDB
2-acetamido-2-Deoxy-D-glucopyranose	HMDB
2-Acetamido-2-deoxy-D-glucose	ChEBI
2-acetamido-2-Deoxy-D-glucose	ChEBI
2-Acetamido-2-deoxyglucose	HMDB

Showing 1 to 10 of 22 entries

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

Chemical Formula

C8H15NO6

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

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
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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Element:

Platelet

Organ and components:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Food and nutrition:

Nutritional supplement

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	C 43.44%; H 6.83%; N 6.33%; O 43.40%	CCD
Melting Point	Mp 205°	CCD
Optical Rotation	[a] 18D +64	CCD

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-943fefe13d3449a92db7	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0f9j-1930000000-388fd70c48f209a58653	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-1fd16b8e8608db3ef657	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-ceed8b621b338130ce76	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-8a3ade37d256b2bd4585	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-943fefe13d3449a92db7	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-0f9j-1930000000-388fd70c48f209a58653	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-1fd16b8e8608db3ef657	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-ceed8b621b338130ce76	Spectrum
GC-MS	N-Acetylglucosamine, non-derivatized, GC-MS Spectrum	splash10-00di-9620000000-8a3ade37d256b2bd4585	Spectrum
Predicted GC-MS	N-Acetylglucosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ue9-6920000000-c07df80c6fb758af9cd2	Spectrum
Predicted GC-MS	N-Acetylglucosamine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-3332900000-ee533266929b5b95ee4d	Spectrum
Predicted GC-MS	N-Acetylglucosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetylglucosamine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9800000000-d2628c9d8baf55923bf5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pb9-9500000000-76ab0b7c683cc252741d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pb9-9400000000-5b6f61c6f220e75c6736	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pb9-9500000000-17fd92d5a45dc38915af	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-ccb575a1c77c8addd5fe	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0pb9-9500000000-bf8c7a4f84891bcf3eb2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-9000000000-f38ecd220da0924d093c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-9400000000-eaa89be4aad99c7a4503	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-3900000000-819a6ad0f73785d9287c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1910000000-723db02c59f390b489a7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0537-9000000000-735f54db3223e736c337	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003e-9600000000-197c8bc76e52b96b9871	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1490000000-40dfe33adabe6ad7a7a8	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0il0-2940000000-880c7b1fb58ed63f0ee2	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9400000000-e1f07558d7921e9f24e1	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05g0-8920000000-d504941e0508d1593f33	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9820000000-753556be259b7e745ba7	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-bad102d081eb3bbc006b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9500000000-2c2b09cb6bfb29039085	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9540000000-a1f7d557237a521d306a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-18eabe9e3d3657888360	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0390000000-3820a7eec5a8c72f49d9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h90-9740000000-db880363194a3979c637	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-9200000000-cdcf015aa799dc7d6d8b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

506227

Phenol-Explorer ID

Not Available

DrugBank ID

DB00141

HMDB ID

HMDB00215

CRC / DFC (Dictionary of Food Compounds) ID

BXT68-E:BXT68-E

EAFUS ID

Not Available

Dr. Duke ID

N-ACETYL-GLUCOSAMINE

BIGG ID

34006

KNApSAcK ID

Not Available

HET ID

NGZ

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

N-Acetylglucosamine

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

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Name	Gene Name	UniProt ID
Acidic mammalian chitinase	CHIA	Q9BZP6
Alpha-N-acetylglucosaminidase	NAGLU	P54802
Beta-hexosaminidase subunit alpha	HEXA	P06865
Beta-hexosaminidase subunit beta	HEXB	P07686
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase	GNE	Q9Y223
Chitotriosidase-1	CHIT1	Q13231
Lysozyme C	LYZ	P61626
Lysozyme-like protein 1	LYZL1	Q6UWQ5
Lysozyme-like protein 2	LYZL2	Q7Z4W2
Lysozyme-like protein 6	LYZL6	O75951