ChemFOnt: Showing chemical card for Chitin (CFc000001855)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:35 UTC

Chemfont ID

CFc000001855

Molecule Identification

Common Name

Chitin

Definition

Chitin is one of the main components in the cell walls of fungi, the exoskeletons of insects and other arthropods (such as crustaceans) as well as fish and frogs. It is a polysaccharide that is constructed from units of acetylglucosamine (more completely, N-acetyl-D-glucose-2-amine). These are linked together in beta-1,4 fashion (in a similar manner to the glucose units which form cellulose). In effect, chitin may be described as cellulose with one hydroxyl group on each monomer replaced by an acetylamine group. This allows for increased hydrogen bonding between adjacent polymers, giving the polymer increased strength. Chitin is the second most abundant polysaccharide in the world (after cellulose). Chitinases break down chitin and are a part of the defence mechanism of mammals against chitin-containing parasites in lower life forms. Under certain circumstances, chitin can act as an allergen. Research using murine models has shown that chitin is a size-dependent microbial-associated molecular pattern (MAMP) that can induce an immunological response via pattern recognition receptors. Medium-sized chitin micro-particles (CMPs) have been shown to induce inflammation, while small-sized CMPs reduce inflammation. Additionally, mammalian chitinases may play a key role in mediating the T-helper 2 cell-driven inflammatory response that is commonly associated with asthma. The high prevalence of asthma among people working with chitinous substances, such as crabs and fungi, suggests that chitin might be an allergen playing a significant role in the development of asthma.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-1,4-Poly-N-acetyl-D-glucosamine	HMDB
beta-1,4-Poly-N-acetyl-delta-glucosamine	HMDB
Poly 2-acetamido-2-deoxy-D-glucose	HMDB
Poly 2-acetamido-2-deoxy-delta-glucose	HMDB
[1,4-(N-Acetyl-beta-D-glucosaminyl)]N	HMDB
[1,4-(N-Acetyl-beta-D-glucosaminyl)]n+1	HMDB
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]N	HMDB
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]n+1	HMDB

Chemical Formula

C₂₈H₄₉N₃O₁₆

Average Molecular Weight

683.6992

Monoisotopic Molecular Weight

683.311282535

IUPAC Name

N-[(2R,4S,5S)-5-({[(2R,4S,5S)-3-acetamido-5-({[(2R,4R,5S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}methyl)-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}methyl)-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional Name

CAS Registry Number

1398-61-4

SMILES

[H][C@@]1(O)OC([H])(CO)[C@@]([H])(COC[C@]2([H])OC([H])(CO)[C@@]([H])(COC[C@]3([H])OC([H])(CO)[C@@]([H])(O)[C@]([H])(O)C3([H])N=C(C)O)[C@]([H])(O)C2([H])N=C(C)O)[C@]([H])(O)C1([H])N=C(C)O

InChI Identifier

InChI=1S/C28H49N3O16/c1-11(35)29-21-19(9-44-8-15-17(5-33)47-28(42)23(25(15)39)31-13(3)37)45-16(4-32)14(24(21)38)7-43-10-20-22(30-12(2)36)27(41)26(40)18(6-34)46-20/h14-28,32-34,38-42H,4-10H2,1-3H3,(H,29,35)(H,30,36)(H,31,37)/t14-,15-,16?,17?,18?,19+,20+,21?,22?,23?,24+,25+,26-,27-,28-/m1/s1

InChI Key

DJHJJVWPFGHIPH-OODMECLYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic nitrogen compound
Primary alcohol
Organic oxide
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Fibroblasts (HMDB: HMDB0003362)

Organ

Cellular substructure

Extracellular (HMDB: HMDB0003362)
Membrane (HMDB: HMDB0003362)

Source

Endogenous

Endogenous (HMDB: HMDB0003362)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (HMDB: HMDB0003362)
Glutamate Metabolism (HMDB: HMDB0003362)
Amino Sugar and Nucleotide Sugar Metabolism III (PathBank: SMP0121303)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Amino Sugar and Nucleotide Sugar Metabolism II (PathBank: SMP0000906)
Amino Sugar and Nucleotide Sugar Metabolism (PathBank: SMP0002331)
Chitin Biosynthesis (PathBank: SMP0094667)

Disease pathway

Tay-Sachs Disease (HMDB: HMDB0003362)
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Homocarnosinosis (PathBank: SMP0120494)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)

Role

Biological role

Human metabolite (HMDB: HMDB0003362)

Industrial application

Vulnerary (HMDB: HMDB0003362)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.17 g/L	ALOGPS
logP	-2	ALOGPS
logP	-7.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	295.29 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	153.69 m³·mol⁻¹	ChemAxon
Polarizability	68.75 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023154

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chitin

METLIN ID

Not Available

PubChem Compound

21252321

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kurita, Keisuke; Koyama, Yoshiyuki; Nishimura, Shinichiro; Kamiya, Mami. Facile preparation of water-soluble chitin from chitosan. Chemistry Letters (1989), (9), 1597-8.

Showing chemical card for Chitin (CFc000001855)

MOL for CFc000001855 (Chitin)

3D MOL for CFc000001855 (Chitin)

3D SDF for CFc000001855 (Chitin)

3D-SDF for CFc000001855 (Chitin)

PDB for CFc000001855 (Chitin)

3D PDB for CFc000001855 (Chitin)

SMILES for CFc000001855 (Chitin)

INCHI for CFc000001855 (Chitin)

Structure for CFc000001855 (Chitin)

3D Structure for CFc000001855 (Chitin)