ChemFOnt: Showing chemical card for N-Acetylmannosamine (CFc000000883)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:24 UTC

Chemfont ID

CFc000000883

Molecule Identification

Common Name

N-Acetylmannosamine

Definition

N-Acetylmannosamine, also known as beta-ManNAcc or β-ManNAc, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Within humans, N-acetylmannosamine participates in a number of enzymatic reactions. In particular, N-acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine, which is catalyzed by the enzyme N-acylglucosamine 2-epimerase. In addition, N-acetylmannosamine and uridine 5'-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In humans, N-acetylmannosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. In the rate-limiting step of the pathway, UDP-GlcNAc is converted into ManNAc by UDP-GlcNAc 2-epimerase, encoded by the epimerase domain of GNE. Improved sialylation after the addition of ManNAc and other supporting ingredients to the culture medium not only increases manufacturing yield, but also improves therapeutic efficacy by increasing solubility, increasing half-life and reducing immunogenicity by reducing the formation of antibodies to the therapeutic glycoprotein When the GNE epimerase kinase does not function correctly in the human body thereby reducing the available ManNAc, it is reasonable to assume that treatment with ManNAc could assist with improving health benefits. There is no available therapy to treat GNE myopathy. ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-ManNAc	ChEBI
N-Acetyl-beta-mannosamine	ChEBI
b-ManNAc	Generator
Β-mannac	Generator
N-Acetyl-b-mannosamine	Generator
N-Acetyl-β-mannosamine	Generator
2-Acetamido-2-deoxy-D-mannopyranose	HMDB
2-Acetamido-2-deoxy-D-mannose	HMDB
ManNAc	HMDB
N-Acetyl-D-mannosamine	HMDB
N-Acetylmannosamine, (D)-isomer	HMDB
N-Acetylmannosamine, (L)-isomer	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Molecular Weight

221.2078

Monoisotopic Molecular Weight

221.089937217

IUPAC Name

N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

N-acetylmannosamine

CAS Registry Number

7772-94-3

SMILES

CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

OVRNDRQMDRJTHS-OZRXBMAMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-mannosamine (CHEBI:63154 )

Functional Ontology

Not Available

Fibroblasts (HMDB: HMDB0001129)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0001129)

Organ

Prostate (HMDB: HMDB0001129)

Excreta

Biofluid or Excreta

Feces (PMID: 22411374)
Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0001129)

Source

Exogenous

Exogenous (HMDB: HMDB0001129)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001129)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (PathBank: SMP0063580)
N-Acetylneuraminate, N-Acetylmannosamine, and N-Acetylglucosamine Degradation (PathBank: SMP0002044)

Disease pathway

Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Tay-Sachs Disease (PathBank: SMP0120545)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	254 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.2	ChemAxon
logS	0.06	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	20.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001129

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028419

KNApSAcK ID

Not Available

Chemspider ID

9271300

KEGG Compound ID

C00645

BioCyc ID

N-ACETYL-D-MANNOSAMINE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

63154

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical & Pharmaceutical Bulletin (1964), 12(5), 615-19.

Showing chemical card for N-Acetylmannosamine (CFc000000883)

MOL for CFc000000883 (N-Acetylmannosamine)

3D MOL for CFc000000883 (N-Acetylmannosamine)

3D SDF for CFc000000883 (N-Acetylmannosamine)

3D-SDF for CFc000000883 (N-Acetylmannosamine)

PDB for CFc000000883 (N-Acetylmannosamine)

3D PDB for CFc000000883 (N-Acetylmannosamine)

SMILES for CFc000000883 (N-Acetylmannosamine)

INCHI for CFc000000883 (N-Acetylmannosamine)

Structure for CFc000000883 (N-Acetylmannosamine)

3D Structure for CFc000000883 (N-Acetylmannosamine)