Bovine Metabolome Database: Showing metabocard for N-Acetyl-D-glucosamine (BMDB0000215)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (21) Show 21 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:51 UTC

Update Date

2020-06-04 20:57:15 UTC

BMDB ID

BMDB0000215

Secondary Accession Numbers

BMDB00215

Metabolite Identification

Common Name

N-Acetyl-D-glucosamine

Description

N-Acetyl-D-glucosamine belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-glucosamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-glucosamine can be biosynthesized from chitobiose; which is catalyzed by the enzyme Beta-hexosaminidase subunit alpha. In addition, N-Acetyl-D-glucosamine can be converted into N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme N-acetyl-D-glucosamine kinase. In cattle, N-acetyl-D-glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-acetamido-2-Deoxyglucose	MeSH
N Acetyl D glucosamine	MeSH
2 acetamido 2 Deoxyglucose	MeSH
2-acetamido-2-Deoxy-D-glucose	MeSH
2 acetamido 2 Deoxy D glucose	MeSH
2-(Acetylamino)-2-deoxy-a-L-glucopyranose	Generator
2-(Acetylamino)-2-deoxy-α-L-glucopyranose	Generator

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

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+/m0/s1

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Lysosome
Membrane
Myelin sheath

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	-2.6	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	20.6 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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0f79-0940000000-0d7d2d612ca41562809e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-001s-9600000000-3de4e51e2205e3ff671f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001j-9000000000-fcf5ccaeb65b9b59825d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0390000000-ce54c5d356ec2fc8ab9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0il0-2950000000-e4e02ffea74d8dfd0810	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9400000000-193b1fdde3c57b9db67a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-9830000000-5464ceae5afcba890084	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ac0-9820000000-78cbfc747ed0209c6806	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-407cae358947a1ac5567	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Lysosome
Membrane
Myelin sheath

Biospecimen Locations

Intestine
Liver
Milk
Neuron
Placenta
Platelet
Prostate Tissue
Ruminal Fluid

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	198.908 (126.578-370.692) uM	Not Specified	Not Specified	Normal	Esperanza Troyano...	details
Milk	Detected and Quantified	506.311 uM	Not Specified	Not Specified	Normal	Johan E. Hoff. De...	details
Milk	Detected and Quantified	230.10 +/- 2.26 uM	Not Specified	Not Specified	Normal	Tommaso R.I. Cata...	details
Milk	Detected and Quantified	238 +/- 90 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	302 +/- 76 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	278 +/- 94 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	351 +/- 34 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	16 uM	Adult	Both	Normal	PMID: 4219266	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11861101

PDB ID

NGZ

ChEBI ID

Not Available

References

Synthesis Reference

Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details

1. Beta-1,4-galactosyltransferase 1

General function:: Involved in alpha-tubulin binding
Specific function:: The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:: B4GALT1
Uniprot ID:: P08037
Molecular weight:: 44843.0

Enzyme Details

2. Beta-1,4-galactosyltransferase 3

General function:: Involved in beta-N-acetylglucosaminylglycopeptide beta-
Specific function:: Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:: B4GALT3
Uniprot ID:: Q5EA87
Molecular weight:: 44371.0

Enzyme Details

3. Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1

General function:: Involved in alpha-1,3-mannosylglycoprotein 2-beta-N-ace
Specific function:: Participates in O-mannosyl glycosylation by catalyzing the addition of N-acetylglucosamine to O-linked mannose on glycoproteins. Catalyzes the synthesis of the GlcNAc(beta1-2)Man(alpha1-)O-Ser/Thr moiety on alpha-dystroglycan and other O-mannosylated proteins, providing the necessary basis for the addition of further carbohydrate moieties. Is specific for alpha linked terminal mannose.
Gene Name:: POMGNT1
Uniprot ID:: Q5EAB6
Molecular weight:: 75077.0

Enzyme Details

4. Lysozyme C, milk isozyme

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: Not Available
Uniprot ID:: Q6B411
Molecular weight:: 16783.0

Enzyme Details

5. Lysozyme C-3

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: LYZ3
Uniprot ID:: Q06284
Molecular weight:: 16317.0

Enzyme Details

6. Lysozyme-like protein 6

General function:: Involved in lysozyme activity
Specific function:: May be involved sperm-egg plasma membrane adhesion and fusion during fertilization. Exhibits bacteriolytic activity in vitro against Micrococcus luteus and Staphylococcus aureus. Shows weak bacteriolytic activity against Gram-positive bacteria at physiological pH. Bacteriolytic activity is pH-dependent, with a maximum at around pH 5.6 (By similarity).
Gene Name:: LYZL6
Uniprot ID:: Q29RT1
Molecular weight:: 16559.0

Enzyme Details

7. N-acetyl-D-glucosamine kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Also has ManNAc kinase activity (By similarity).
Gene Name:: NAGK
Uniprot ID:: Q3SZM9
Molecular weight:: 37268.0

Enzyme Details

8. Lysozyme C, non-stomach isozyme

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: LYS
Uniprot ID:: P80189
Molecular weight:: 16476.0

Enzyme Details

9. Lysozyme C, intestinal isozyme

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: Not Available
Uniprot ID:: Q6B410
Molecular weight:: 16391.0

Enzyme Details

10. N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase

General function:: Involved in N-acetylglucosamine-1-phosphodiester alpha-
Specific function:: Catalyzes the second step in the formation of the mannose 6-phosphate targeting signal on lysosomal enzyme oligosaccharides by removing GlcNAc residues from GlcNAc-alpha-P-mannose moieties, which are formed in the first step. Also hydrolyzes UDP-GlcNAc, a sugar donor for Golgi N-acetylglucosaminyltransferases.
Gene Name:: NAGPA
Uniprot ID:: P68827
Molecular weight:: 57223.0

Enzyme Details

11. Lysozyme C-1

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: LYZ1
Uniprot ID:: Q06285
Molecular weight:: 16279.0

Enzyme Details

12. Lysozyme C, tracheal isozyme

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: Not Available
Uniprot ID:: Q27996
Molecular weight:: 15929.0

Enzyme Details

13. Lysozyme C

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: LYZ1
Uniprot ID:: P04421
Molecular weight:: 16373.0

Enzyme Details

14. Lysozyme-like protein 1

General function:: Involved in lysozyme activity
Specific function:: Not Available
Gene Name:: LYZL1
Uniprot ID:: A0JNM6
Molecular weight:: 16779.0

Enzyme Details

15. Sperm acrosome-associated protein 5

General function:: Involved in lysozyme activity
Specific function:: Not Available
Gene Name:: SPACA5
Uniprot ID:: Q32PD6
Molecular weight:: 17580.0

Enzyme Details

16. Lysozyme C-2

General function:: Involved in lysozyme activity
Specific function:: Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name:: LYZ2
Uniprot ID:: Q06283
Molecular weight:: 16304.0

Enzyme Details

17. Collectin-43

General function:: Carbohydrate transport and metabolism
Specific function:: Lectin that binds to various sugars: mannose = ManNAc > fucose > GlcNAc > glucose = maltose > galactose > lactose > GalNAc. Could play a role in immune defense.
Gene Name:: CL43
Uniprot ID:: P42916
Molecular weight:: 33616.0

Enzyme Details

18. Conglutinin

General function:: Carbohydrate transport and metabolism
Specific function:: Calcium-dependent lectin-like protein which binds to a yeast cell wall extract and immune complexes through the complement component (C3bi). It is capable of binding non-reducing terminal N-acetylglucosamine, mannose, and fucose residues.
Gene Name:: CGN1
Uniprot ID:: P23805
Molecular weight:: 37995.0

Enzyme Details

19. Mannose-binding protein C

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent lectin involved in innate immune defense. Binds mannose, fucose and N-acetylglucosamine on different microorganisms and activates the lectin complement pathway. Binds to late apoptotic cells, as well as to apoptotic blebs and to necrotic cells, but not to early apoptotic cells, facilitating their uptake by macrophages (By similarity).
Gene Name:: MBL
Uniprot ID:: O02659
Molecular weight:: 26471.0

Enzyme Details

20. Ficolin-2

General function:: Involved in receptor binding
Specific function:: May function in innate immunity through activation of the lectin complement pathway. Calcium-dependent and GlcNAc-binding lectin (By similarity).
Gene Name:: FCN2
Uniprot ID:: Q5I2E5
Molecular weight:: 35339.0

Enzyme Details

21. Sperm acrosome membrane-associated protein 3

General function:: Involved in lysozyme activity
Specific function:: Sperm surface membrane protein that may be involved in sperm-egg plasma membrane adhesion and fusion during fertilization. It could be a potential receptor for the egg oligosaccharide residue N-acetylglucosamine, which is present in the extracellular matrix over the egg plasma membrane. The processed form has no detectable bacteriolytic activity in vitro (By similarity).
Gene Name:: SPACA3
Uniprot ID:: A6QQ77
Molecular weight:: 18099.0

Showing metabocard for N-Acetyl-D-glucosamine (BMDB0000215)

Structure for BMDB0000215 (N-Acetyl-D-glucosamine)

Enzymes