N-Acetylglucosamine
Athanor · official
C8H15NO6 · 221.21 g/mol
IUPAC name: N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Also called GlcNAc, NAG, chitin unit, peptidoglycan unit, N-acetyl-D-glucosamine
Names and identifiers
- IUPAC name
- N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
- Synonyms
- GlcNAc, NAG, chitin unit
+ 40 more
peptidoglycan unit, N-acetyl-D-glucosamine, 2-acetamido-2-deoxy-D-glucopyranose, 2-Deoxy-2-Acetamido-D-Glucopyranose, n-acetyl-glucosamine, 2-acetamido-2-deoxy-glucose, 2-Deoxy-2-Acetamido-Glucose, 2-Acetamido-2-Deoxy-Glucopyranose, 2-Deoxy-2-Acetamido-Glucopyranose, 2-acetamido-2-deoxy-glucopyranoside, 2-Deoxy-2-Acetamido-Glucopyranoside, 2-acetamido-2-deoxy-D-glucopyranoside, 2-Deoxy-2-Acetamido-D-Glucopyranoside, 2-Acetamido-2-Deoxy-D-Glucose, 2-Deoxy-2-Acetamido-D-Glucose, D-GlcNAc, GlcNAc (SNFG), N-Acetyl-D-Glucosamine, SNFG:GlcNAc, N-Acetylchitosamine, N-Acetyl-D-glucosamine-Agarose, N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide, N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide, NAcGlc, CHEBI:506227, 2-(Acetylamino)-2-deoxy-D-glucopyranose, Glucosamine EP Impurity A, SMR000857242, C8H15NO6, N-Acetyl-2-amino-2-deoxy-D-glucose, 2-(Acetylamino)-2-deoxyhexopyranose #, Epitope ID:137340, MLS001333127, MLS001333128, SCHEMBL468802, 2-(Acetylamino)-2-deoxyhexose, CHEMBL240524, orb1221812, SCHEMBL3709060, N-Acetylglucosamine cyclized form
- Molecular formula
- C8H15NO6
- Empirical formula
- C8H15NO6
- Molecular weight
- 221.21 g/mol
- Exact mass
- 221.08994
- CAS number
- 7512-17-6
- PubChem CID
- 439174
- Canonical SMILES
- CC(=O)NC1C(C(C(OC1O)CO)O)O
- Isomeric SMILES
- CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](OC1O)CO)O)O
- InChI
- 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
- InChIKey
- OVRNDRQMDRJTHS-RTRLPJTCSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 15
- Rings
- 1
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0.88
- H-bond donors
- 5
- H-bond acceptors
- 6
- Rotatable bonds
- 2
- TPSA (Ų)
- 119.3 computed here · PubChem 119
- Formal charge
- 0
- XLogP3
- -1.7 PubChem
- Complexity
- 235 PubChem
- Stereocenters
- 4 defined, 1 undefinedCIP: C5: R · C6: undefined · C9: R · C12: S · C14: R
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C43.44%
- H6.84%
- N6.33%
- O43.40%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -3.08 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- 0.86 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.63 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 221.21
- log P ≤ 5 (Crippen): -3.08
- H-bond donors ≤ 5: 5
- H-bond acceptors ≤ 10: 6
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: 001Chemical, CATO Research Chemicals Inc., Molport.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRSpectraBase
- 13C NMRSpectraBase
- GC-MSHuman Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive)
- MS-MSHuman Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative)
- LC-MSMassBank Europe (Agilent 6530 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Agilent 6530 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (impact II · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (impact II · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (impact II · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (Q-Exactive Orbitrap, Thermo Scientfic; Ultimate 3000 HPLC, Thermo Scientfic · LC-ESI-QFT · NEGATIVE)
- Other MSMassBank of North America (MoNA) (positive) · MassBank of North America (MoNA) (qTof · positive) · MassBank of North America (MoNA) (qTof · negative)
- ATR-IRSpectraBase (Bio-Rad FTS · ATR-Neat (DuraSamplIR II))
- RamanSpectraBase
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.