UDP-N-acetylglucosamine (C17H27N3O17P2): structure, properties and hazards

Names and identifiers

IUPAC name: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
Synonyms: UDP-GlcNAc, hexosamine pathway, O-GlcNAc donor
+ 37 more
URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE, RefChem:901487, UDP-N-acetyl-D-glucosamine, UDP-acetylglucosamine, UPPAG, UDP-alpha-D-N-acetylglucosamine, UDP-N-acetyl-alpha-D-glucosamine, [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate, UDP-acetyl-D-glucosamine, (2R,3R,4R,5S,6R)-3-(acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name), UD1, UDP-a-D-N-acetylglucosamine, UDP-N-acetyl-alphaD-glucosamine, Uridine diphosphoacetylglucosamine, UDP-N-acetyl-glucosamine, Udpx, Uridine 5'-diphospho-N-acetylglucosamine, Uridine diphospho-N-acetyl-D-glucosamine, N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide, Uridine diphosphate N-acetyl-D-glucosamine, Uridine diphospho-2-acetamido-2-deoxy-D-glucose, UDP N-acetyl-glucosamine, UDP-acetyl-delta-glucosamine, CHEMBL388154, GTPL1779, orb3141781, SCHEMBL1521296, UDP-N-acetyl-delta-glucosamine, CHEBI:16264, LFTYTUAZOPRMMI-CFRASDGPSA-N, UDP N-acetyl-alpha-D-glucosamine, DTXSID101377936, UDP-alpha-delta-N-acetylglucosamine, LMSL01010002, DB03397, MU04393, TN11381
Molecular formula: C₁₇H₂₇N₃O₁₇P₂
Empirical formula: C₁₇H₂₇N₃O₁₇P₂
Molecular weight: 607.4 g/mol
Exact mass: 607.08157
CAS number: 528-04-1
PubChem CID: 445675
Canonical SMILES: CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
InChI: InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
InChIKey: LFTYTUAZOPRMMI-CFRASDGPSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 39
Rings: 3
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.71
H-bond donors: 9
H-bond acceptors: 15 computed here · PubChem 17
Rotatable bonds: 10
TPSA (Å²): 305.9 computed here · PubChem 300
Formal charge: 0
XLogP3: -6.6 PubChem
Complexity: 1080 PubChem
Stereocenters: 9 defined, 2 undefinedCIP: C5: R · C6: R · P8: undefined · P12: undefined · C17: R · C19: R · C28: R · C30: S · C33: R · C36: S · C38: 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

C33.62%
H4.48%
N6.92%
O44.78%
P10.20%

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: -4.65 Crippen (Wildman and Crippen 1999)
log S (water solubility): -0.13 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 4.91 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 607.36
log P ≤ 5 (Crippen): -4.65
H-bond donors ≤ 5: 9
H-bond acceptors ≤ 10: 15

Breaks 3 of the 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: InvivoChem, Alfa Chemistry, BLD Pharm.

Always read the supplier’s safety data sheet before working with it.

Spectra

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]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[3]MassBank of North America (MoNA) · CC BY 4.0 · 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.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.

Isomers in the library

UDP-N-acetylgalactosamine