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).
In the Vinony graph
Vinony's link graph records 9 inbound references to N-Acetylmannosamine, and connects out to N-acetylneuraminic acid, carbohydrate and glucose.
Vinony files it under Acetamides, Acetyl compounds and Chembox image size set.
Vinony links it to 9 Wikipedia language editions.
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.