Structure via PubChem · Public domain (PubChem)
N-Acetylmannosamine
Sign in to save'''N-Acetylmannosamine''' is a hexosamine monosaccharide. It is a neutral, stable naturally occurring compound. N-Acetylmannosamine is also known as N-Acetyl-D-mannosamine monohydrate, (which has the CAS Registry Number: 676347-48-1), N-Acetyl-D-mannosamine which can be abbreviated to ManNAc or, less commonly, NAM). ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid) (Figure 1). Sialic acids are the negatively charged, terminal monosaccharides of carbohydrate chains that are attached to glycoproteins and glycolipids (glycans).
Chemical data
- Formula
- C8H15NO6
- Molecular weight
- 221.21 g/mol
- IUPAC name
- N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
- SMILES
- CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O
- InChIKey
- OVRNDRQMDRJTHS-OZRXBMAMSA-N
- XLogP
- -1.7
- Polar surface area
- 119 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 221.0899372
Show 4 more facts
- chemical formula
- C₈H₁₅NO₆
- isomeric SMILES
- O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O
- canonical SMILES
- CC(=O)NC1C(C(C(OC1O)CO)O)O
- Commons category
- N-Acetylmannosamine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Biological role of ManNAc
- Synthesis
- Uses
- Sialylation of recombinant proteins
- Therapeutic potential
- GNE myopathy
- Kidney diseases
- References
'''N-Acetylmannosamine''' is a hexosamine monosaccharide. It is a neutral, stable naturally occurring compound. N-Acetylmannosamine is also known as N-Acetyl-D-mannosamine monohydrate, (which has the CAS Registry Number: 676347-48-1), N-Acetyl-D-mannosamine which can be abbreviated to ManNAc or, less commonly, NAM). ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid) (Figure 1). Sialic acids are the negatively charged, terminal monosaccharides of carbohydrate chains that are attached to glycoproteins and glycolipids (glycans).
== Biological role of ManNAc == ManNAc is the first committed biological precursor of Neu5Ac.
Excerpted from Wikipedia’s “N-Acetylmannosamine” article, available under the CC BY-SA 4.0 licence.