MiMeDB: Showing metabocard for N-acetyl-D-hexosamine (MMDBc0056137)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:17:44 UTC

Update Date

2025-10-07 16:04:20 UTC

Metabolite ID

MMDBc0056137

Metabolite Identification

Common Name

N-acetyl-D-hexosamine

Description

N-acetyl-D-hexosamine is a member of the amino sugar class of carbohydrates, specifically a derivative of hexosamine. Its chemical structure features an acetyl group attached to the nitrogen of the amino group on the hexose ring, making it a key component in various biochemical pathways. N-acetyl-D-hexosamine plays a crucial role in the synthesis of glycoproteins and glycolipids, serving as a building block for complex carbohydrates. It is involved in metabolic pathways such as the production of UDP-N-acetyl-D-hexosamine, which is essential for glycosylation processes. The first enzyme in this pathway, N-acetyl-D-hexosamine oxidase, has been characterized from Ralstonia solanacearum and shows high activity with N-acetylglucosamine and N-acetylgalactosamine (PMID:34709726 ). Additionally, N-acetyl-D-hexosamine is implicated in the synthesis of Galacto-N-biose derivatives via a two-enzyme system from Bifidobacterium infantis (PMID:26023910 ) and serves as a substrate for phosphorylases that facilitate the production of fluorinated Thomsen-Friedenreich antigens (PMID:23241945 ). Its structural isomers, including N-acetyl-D-glucosamine and N-acetyl-D-galactosamine, have also been studied for their vibrational signatures (PMID:28050874 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222172D          

 20 20  0  0  1  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  1  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  4  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
  4 16  1  6  0  0  0
 17  5  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056137

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C1(O)O[C@]([H])(CO)C([H])(O)C([H])(O)C1([H])N=C(C)O

> <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-BKJPEWSUSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.209

> <EXACT_MASS>
221.089937207

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.671293364301924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid

> <JCHEM_LOGP>
-2.400970284666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.71277465937263

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.729937166971195

> <JCHEM_PKA_STRONGEST_BASIC>
1.4620643976553511

> <JCHEM_POLAR_SURFACE_AREA>
122.74000000000002

> <JCHEM_REFRACTIVITY>
47.5464

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4   10                                                       
CONECT    3    1    9   11                                                  
CONECT    4    2    6   15   16                                             
CONECT    5    7    8    9   17                                             
CONECT    6    4    7   12   18                                             
CONECT    7    5    6   13   19                                             
CONECT    8    5   14   15   20                                             
CONECT    9    3    5                                                       
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    4    8                                                       
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Synonyms

Value	Source
N-Acetyl-D-hexosamines	ChEBI
N-Acetylhexosamine	ChEBI
N-Acetylhexosamines	ChEBI

Molecular Formula

C₈H₁₅NO₆

Average Mass

221.209

Monoisotopic Mass

221.089937207

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C1(O)O[C@]([H])(CO)C([H])(O)C([H])(O)C1([H])N=C(C)O

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-BKJPEWSUSA-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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.4	ChemAxon
pKa (Strongest Acidic)	5.73	ChemAxon
pKa (Strongest Basic)	1.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	20.67 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	421.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	314.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	47.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	234.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	288.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	253.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	543.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	679.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	658.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	149.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	358.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	164.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	43.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	310.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	558.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	62.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	222.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	690.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	543.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-acetyl-D-hexosamine_TMS_1	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O	standard non polar	2025-10-24	1320.16
Gas Chromatography	N-acetyl-D-hexosamine_TMS_2	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O	standard non polar	2025-10-24	2232.79
Gas Chromatography	N-acetyl-D-hexosamine_TMS_3	CC(O)=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O	standard non polar	2025-10-24	2276.49
Gas Chromatography	N-acetyl-D-hexosamine_TMS_4	CC(O)=NC1C(O)O[C@H](CO)C(O)C1O[Si](C)(C)C	standard non polar	2025-10-24	1514.97
Gas Chromatography	N-acetyl-D-hexosamine_TMS_5	CC(=NC1C(O)O[C@H](CO)C(O)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	2004.52
Gas Chromatography	N-acetyl-D-hexosamine_TMS_6	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	2004.08
Gas Chromatography	N-acetyl-D-hexosamine_TMS_7	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O	standard non polar	2025-10-24	1660.52
Gas Chromatography	N-acetyl-D-hexosamine_TMS_8	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O	standard non polar	2025-10-24	1810.49
Gas Chromatography	N-acetyl-D-hexosamine_TMS_9	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O[Si](C)(C)C	standard non polar	2025-10-24	1504.41
Gas Chromatography	N-acetyl-D-hexosamine_TMS_10	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	2248.3
Gas Chromatography	N-acetyl-D-hexosamine_TMS_11	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O	standard non polar	2025-10-24	2170.45
Gas Chromatography	N-acetyl-D-hexosamine_TMS_12	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C	standard non polar	2025-10-24	2253.28
Gas Chromatography	N-acetyl-D-hexosamine_TMS_13	CC(=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	2015.55
Gas Chromatography	N-acetyl-D-hexosamine_TMS_14	CC(O)=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard non polar	2025-10-24	2010.22
Gas Chromatography	N-acetyl-D-hexosamine_TMS_15	CC(=NC1C(O)O[C@H](CO)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1625.57
Gas Chromatography	N-acetyl-D-hexosamine_TMS_16	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	1903.59
Gas Chromatography	N-acetyl-D-hexosamine_TMS_17	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	1461.34
Gas Chromatography	N-acetyl-D-hexosamine_TMS_18	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2607.69
Gas Chromatography	N-acetyl-D-hexosamine_TMS_19	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O	standard non polar	2025-10-24	2017.43
Gas Chromatography	N-acetyl-D-hexosamine_TMS_20	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C	standard non polar	2025-10-24	1509.45
Gas Chromatography	N-acetyl-D-hexosamine_TMS_21	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard non polar	2025-10-24	1965.19
Gas Chromatography	N-acetyl-D-hexosamine_TMS_22	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	1883.41
Gas Chromatography	N-acetyl-D-hexosamine_TMS_23	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2139.97
Gas Chromatography	N-acetyl-D-hexosamine_TMS_24	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard non polar	2025-10-24	1973.85
Gas Chromatography	N-acetyl-D-hexosamine_TMS_25	CC(=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2372.98
Gas Chromatography	N-acetyl-D-hexosamine_TMS_26	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard non polar	2025-10-24	1843.64
Gas Chromatography	N-acetyl-D-hexosamine_TMS_27	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	886.56
Gas Chromatography	N-acetyl-D-hexosamine_TMS_28	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1945.42
Gas Chromatography	N-acetyl-D-hexosamine_TMS_29	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard non polar	2025-10-24	2672.0
Gas Chromatography	N-acetyl-D-hexosamine_TMS_30	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1508.45
Gas Chromatography	N-acetyl-D-hexosamine_TMS_31	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1754.41
Gas Chromatography	N-acetyl-D-hexosamine_TMS_1	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O	standard polar	2025-10-24	1982.1
Gas Chromatography	N-acetyl-D-hexosamine_TMS_2	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O	standard polar	2025-10-24	1806.16
Gas Chromatography	N-acetyl-D-hexosamine_TMS_3	CC(O)=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O	standard polar	2025-10-24	1753.77
Gas Chromatography	N-acetyl-D-hexosamine_TMS_4	CC(O)=NC1C(O)O[C@H](CO)C(O)C1O[Si](C)(C)C	standard polar	2025-10-24	2352.54
Gas Chromatography	N-acetyl-D-hexosamine_TMS_5	CC(=NC1C(O)O[C@H](CO)C(O)C1O)O[Si](C)(C)C	standard polar	2025-10-24	2311.5
Gas Chromatography	N-acetyl-D-hexosamine_TMS_6	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O)O[Si](C)(C)C	standard polar	2025-10-24	2255.85
Gas Chromatography	N-acetyl-D-hexosamine_TMS_7	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O	standard polar	2025-10-24	1602.09
Gas Chromatography	N-acetyl-D-hexosamine_TMS_8	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O	standard polar	2025-10-24	1793.96
Gas Chromatography	N-acetyl-D-hexosamine_TMS_9	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O[Si](C)(C)C	standard polar	2025-10-24	2308.63
Gas Chromatography	N-acetyl-D-hexosamine_TMS_10	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O)O[Si](C)(C)C	standard polar	2025-10-24	2313.89
Gas Chromatography	N-acetyl-D-hexosamine_TMS_11	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O	standard polar	2025-10-24	2334.12
Gas Chromatography	N-acetyl-D-hexosamine_TMS_12	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C	standard polar	2025-10-24	2009.42
Gas Chromatography	N-acetyl-D-hexosamine_TMS_13	CC(=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard polar	2025-10-24	2646.44
Gas Chromatography	N-acetyl-D-hexosamine_TMS_14	CC(O)=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard polar	2025-10-24	2058.21
Gas Chromatography	N-acetyl-D-hexosamine_TMS_15	CC(=NC1C(O)O[C@H](CO)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2294.22
Gas Chromatography	N-acetyl-D-hexosamine_TMS_16	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O)O[Si](C)(C)C	standard polar	2025-10-24	1932.79
Gas Chromatography	N-acetyl-D-hexosamine_TMS_17	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard polar	2025-10-24	1249.39
Gas Chromatography	N-acetyl-D-hexosamine_TMS_18	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1891.74
Gas Chromatography	N-acetyl-D-hexosamine_TMS_19	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O	standard polar	2025-10-24	1252.66
Gas Chromatography	N-acetyl-D-hexosamine_TMS_20	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C	standard polar	2025-10-24	2667.85
Gas Chromatography	N-acetyl-D-hexosamine_TMS_21	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard polar	2025-10-24	1259.73
Gas Chromatography	N-acetyl-D-hexosamine_TMS_22	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard polar	2025-10-24	2008.89
Gas Chromatography	N-acetyl-D-hexosamine_TMS_23	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2625.59
Gas Chromatography	N-acetyl-D-hexosamine_TMS_24	CC(O)=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard polar	2025-10-24	2226.23
Gas Chromatography	N-acetyl-D-hexosamine_TMS_25	CC(=NC1C(O)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2801.21
Gas Chromatography	N-acetyl-D-hexosamine_TMS_26	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C	standard polar	2025-10-24	1948.63
Gas Chromatography	N-acetyl-D-hexosamine_TMS_27	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2110.67
Gas Chromatography	N-acetyl-D-hexosamine_TMS_28	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2102.93
Gas Chromatography	N-acetyl-D-hexosamine_TMS_29	CC(O)=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	standard polar	2025-10-24	2325.69
Gas Chromatography	N-acetyl-D-hexosamine_TMS_30	CC(=NC1C(O)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2464.55
Gas Chromatography	N-acetyl-D-hexosamine_TMS_31	CC(=NC1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2701.72

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

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

388949

KEGG Compound ID

C03136

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439916

PDB ID

Not Available

ChEBI ID

21601

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-acetyl-D-hexosamine (MMDBc0056137)

MOL for #<Metabolite:0x00007f9acb818c48>

3D MOL for #<Metabolite:0x00007f9acb818c48>

3D SDF for #<Metabolite:0x00007f9acb818c48>

3D-SDF for #<Metabolite:0x00007f9acb818c48>

PDB for #<Metabolite:0x00007f9acb818c48>

3D PDB for #<Metabolite:0x00007f9acb818c48>

SMILES for #<Metabolite:0x00007f9acb818c48>

INCHI for #<Metabolite:0x00007f9acb818c48>

Structure for #<Metabolite:0x00007f9acb818c48>

3D Structure for #<Metabolite:0x00007f9acb818c48>