N-Acetylneuraminic acid
Athanor · official
C11H19NO9 · 309.27 g/mol
IUPAC name: (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Also called sialic acid, Neu5Ac, NANA, neuraminic acid
Names and identifiers
- IUPAC name
- (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
- Synonyms
- sialic acid, Neu5Ac, NANA
+ 37 more
neuraminic acid, N-acetyl-beta-neuraminic acid, beta-Neu5Ac, TIP79W5HPN, CHEBI:45744, N-acetyl-beta-D-neuraminic acid, DTXSID80864309, (-)-N-acetyl-beta-neuraminic acid, GlyTouCan:G76571JT, RefChem:1048431, DTXCID401324324, G76571JT, N-acetylneuramic acid, N-Acetyl-D-neuraminic acid, 5-N-ACETYL-BETA-D-NEURAMINIC ACID, BETA-SIALIC ACID, Lactaminic acid, Acetylneuraminic acid, MFCD00006620, (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid, (2S,4S,5R,6R)-5-Acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid, N-Acetylsialic acid, 5-N-Acetyl-D-neuraminic acid, CHEMBL165084, 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Neuraminic acid, N-acetyl-, C11H19NO9, 5-acetamido-3,5-dideoxy-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid, O-sialic acid, (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid, NAN, SLB, 5-N-Acetylneuraminic acid, UNII-TIP79W5HPN, Lactaminate, Sialomucin, aceneuramic-acid
- Molecular formula
- C11H19NO9
- Empirical formula
- C11H19NO9
- Molecular weight
- 309.27 g/mol
- Exact mass
- 309.10598
- CAS number
- 131-48-6
- PubChem CID
- 445063
- Canonical SMILES
- CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
- Isomeric SMILES
- CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O
- InChI
- InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
- InChIKey
- SQVRNKJHWKZAKO-PFQGKNLYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 21
- Rings
- 1
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0.82
- H-bond donors
- 7
- H-bond acceptors
- 8 computed here · PubChem 9
- Rotatable bonds
- 5
- TPSA (Ų)
- 176.8 computed here · PubChem 177
- Formal charge
- 0
- XLogP3
- -3.5 PubChem
- Complexity
- 403 PubChem
- Stereocenters
- 6 definedCIP: C5: R · C6: S · C9: S · C15: R · C16: R · C18: 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
- C42.72%
- H6.19%
- N4.53%
- O46.56%
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
- -3.87 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- 1.01 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 4.21 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 309.27
- log P ≤ 5 (Crippen): -3.87
- H-bond donors ≤ 5: 7
- H-bond acceptors ≤ 10: 8
Breaks 1 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: Acmec Biochemical, Amerigo Scientific, EvitaChem.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water) · SpectraBase
- 13C NMRSpectraBase
- 15N NMRSpectraBase
- 1H-1H NMRHuman Metabolome Database (HMDB)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- GC-MSHuman Metabolome Database (HMDB) (GC-MS) · Human Metabolome Database (HMDB) (GC-MS) · Human Metabolome Database (HMDB) (GC-MS) · MassBank of North America (MoNA) (GC-MS) · MassBank of North America (MoNA) (GC-MS) · MassBank of North America (MoNA) (GC-MS)
- MS-MSHuman Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · 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 (Agilent 6530 QTOF · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Thermo Scientific Q-Exactive Focus · LC-ESI-ITFT · NEGATIVE) · MassBank Europe (Thermo Scientific Q-Exactive Focus · LC-ESI-ITFT · NEGATIVE) · MassBank Europe (Thermo Scientific Q-Exactive Focus · LC-ESI-ITFT · NEGATIVE)
- Other MSMassBank of North America (MoNA) (ESI-QTOF · ESI · positive) · MassBank of North America (MoNA) (ESI-QTOF · ESI · positive) · MassBank of North America (MoNA) (ESI-QTOF · ESI · positive)
- FTIRSpectraBase (KBr WAFER)
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]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [4]MassBank Europe · 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.