ChemFOnt: Showing chemical card for Chitosan (CFc000001870)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:37 UTC

Chemfont ID

CFc000001870

Molecule Identification

Common Name

Chitosan

Definition

Chitosan is a linear polysaccharide composed of randomly distributed beta(1->4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). Chitosan has a number of commercial and possible biomedical uses. It can be used in agriculture as a seed treatment and biopesticide, helping plants to fight off fungal infections. In winemaking, it can be used as a fining agent, also helping to prevent spoilage. In industry, it can be used in a self-healing polyurethane paint coating. In medicine, it is useful in bandages to reduce bleeding and as an antibacterial agent; it can also be used to help deliver drugs through the skin. Chitosan is produced commercially by deacetylation of chitin, which is the structural element in the exoskeleton of crustaceans (such as crabs and shrimp) and cell walls of fungi. It is used in hydrogel and to treat wounds. Chitosan can also be used in water processing engineering as a part of a filtration process. Chitosan causes the fine sediment particles to bind together and is subsequently removed with the sediment during sand filtration. Chitosan also removes phosphorous, heavy minerals, and oils from the water. Chitosan is an important additive in the filtration process. Sand filtration apparently can remove up to 50% of the turbidity alone while the Chitosan with sand filtration removes up to 99% turbidity.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-1,4-Poly-D-glucosamine	HMDB
beta-1,4-Poly-delta-glucosamine	HMDB
Chicol	HMDB
Chitopearl 3510	HMDB
Chitopearl BC 3000	HMDB
Chitopearl BCW 2500	HMDB
Chitopearl BCW 3000	HMDB
Chitopearl BCW 3500	HMDB
Chitopearl BCW 3505	HMDB
Chitopearl BCW 3507	HMDB
CTA 4	HMDB
Deacetylchitin	HMDB
Flonac C	HMDB
Flonac N	HMDB
Kimitsu chitosan F	HMDB
Kimitsu chitosan F 2	HMDB
Kimitsu chitosan H	HMDB
Kimitsu chitosan L	HMDB
Kimitsu chitosan m	HMDB
Kytex H	HMDB
Kytex m	HMDB
Poliglusam	HMDB
Sea cure F	HMDB
Sea cure plus	HMDB
YEA	HMDB
N-[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6S)-5-amino-6-{[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]methoxycarboximidate	HMDB
Chitosan	MeSH

Chemical Formula

C₅₆H₁₀₃N₉O₃₉

Average Molecular Weight

1526.4539

Monoisotopic Molecular Weight

1525.635314599

IUPAC Name

methyl N-[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6S)-5-amino-6-{[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate

Traditional Name

chitosan

CAS Registry Number

9012-76-4

SMILES

COC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7N)[C@H](O)[C@H]6N)[C@H](O)[C@H]5N)[C@H](O)[C@H]4N)[C@H](O)[C@H]3N)[C@H](O)[C@H]2N)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](N)[C@H](O[C@H]2[C@H](O)[C@@H](N)[C@H](O)O[C@@H]2CO)O[C@@H]1CO

InChI Identifier

InChI=1S/C56H103N9O39/c1-87-56(86)65-28-38(84)46(19(10-74)96-55(28)104-45-18(9-73)95-49(27(64)37(45)83)97-39-12(3-67)88-47(85)20(57)31(39)77)103-54-26(63)36(82)44(17(8-72)94-54)102-53-25(62)35(81)43(16(7-71)93-53)101-52-24(61)34(80)42(15(6-70)92-52)100-51-23(60)33(79)41(14(5-69)91-51)99-50-22(59)32(78)40(13(4-68)90-50)98-48-21(58)30(76)29(75)11(2-66)89-48/h11-55,66-85H,2-10,57-64H2,1H3,(H,65,86)/t11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48+,49+,50+,51+,52+,53+,54+,55+/m1/s1

InChI Key

FLASNYPZGWUPSU-SICDJOISSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
Aminoglycoside core
Glycosyl compound
O-glycosyl compound
Amino saccharide
Oxane
Methylcarbamate
Carbamic acid ester
1,2-aminoalcohol
Secondary alcohol
Hemiacetal
Carbonic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Primary alcohol
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Alcohol
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Epidermis (HMDB: HMDB0003404)

Cell

Fibroblasts (HMDB: HMDB0003404)
Neuron (HMDB: HMDB0003404)

Hematocyte

Platelet (HMDB: HMDB0003404)

Cellular substructure

Cytoplasm (HMDB: HMDB0003404)

Source

Exogenous

Exogenous (HMDB: HMDB0003404)

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: HMDB0003404)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	69.3 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-18	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	8	ChemAxon
Hydrogen Acceptor Count	46	ChemAxon
Hydrogen Donor Count	29	ChemAxon
Polar Surface Area	808 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	321.21 m³·mol⁻¹	ChemAxon
Polarizability	144.92 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0003404

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015634

KNApSAcK ID

Not Available

Chemspider ID

64870

KEGG Compound ID

C00734

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chitosan

METLIN ID

Not Available

PubChem Compound

71853

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Rashad, Mona M.; Abdou, Hala M.; Mahmoud, Abeer E. Production of chitosan from Pleurotus ostreatus by solid state fermentation. AFS, Advances in Food Sciences (2007), 29(1), 21-26.

Showing chemical card for Chitosan (CFc000001870)

MOL for CFc000001870 (Chitosan)

3D MOL for CFc000001870 (Chitosan)

3D SDF for CFc000001870 (Chitosan)

3D-SDF for CFc000001870 (Chitosan)

PDB for CFc000001870 (Chitosan)

3D PDB for CFc000001870 (Chitosan)

SMILES for CFc000001870 (Chitosan)

INCHI for CFc000001870 (Chitosan)

Structure for CFc000001870 (Chitosan)

3D Structure for CFc000001870 (Chitosan)