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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 19:21:29 UTC
Update Date2021-09-14 15:45:59 UTC
HMDB IDHMDB0003362
Secondary Accession Numbers
  • HMDB03362
Metabolite Identification
Common NameChitin
DescriptionChitin 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
Thumb
Synonyms
Chemical FormulaC24H41N3O16
Average Molecular Weight627.5928
Monoisotopic Molecular Weight627.248682279
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number1398-61-4
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(C)=O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O
InChI Identifier
InChI=1S/C24H41N3O16/c1-7(31)25-13-18(36)20(11(5-29)39-22(13)38)42-24-15(27-9(3)33)19(37)21(12(6-30)41-24)43-23-14(26-8(2)32)17(35)16(34)10(4-28)40-23/h10-24,28-30,34-38H,4-6H2,1-3H3,(H,25,31)(H,26,32)(H,27,33)/t10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+,24+/m1/s1
InChI KeyWZZVUHWLNMNWLW-VFCSDQTKSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility31 g/LALOGPS
logP-2.5ALOGPS
logS-0.92ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Intestine
  • Spleen
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04194
Phenol Explorer Compound IDNot Available
FooDB IDFDB023154
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChitin
METLIN IDNot Available
PubChem Compound444514
PDB IDNot Available
ChEBI ID71404
Food Biomarker OntologyNot Available
VMH IDM01436
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKurita, Keisuke; Koyama, Yoshiyuki; Nishimura, Shinichiro; Kamiya, Mami. Facile preparation of water-soluble chitin from chitosan. Chemistry Letters (1989), (9), 1597-8.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded. Also has ManNAc kinase activity.
Gene Name:
NAGK
Uniprot ID:
Q9UJ70
Molecular weight:
42037.295
General function:
Involved in chitin binding
Specific function:
Degrades chitin and chitotriose. May participate in the defense against nematodes, fungi and other pathogens. Plays a role in T-helper cell type 2 (Th2) immune response. Contributes to the response to IL-13 and inflammation in response to IL-13. Stimulates chemokine production by pulmonary epithelial cells. Protects lung epithelial cells against apoptosis and promotes phosphorylation of AKT1. Its function in the inflammatory response and in protecting cells against apoptosis is inhibited by allosamidin, suggesting that the function of this protein depends on carbohydrate binding.
Gene Name:
CHIA
Uniprot ID:
Q9BZP6
Molecular weight:
Not Available
General function:
Involved in chitin binding
Specific function:
Degrades chitin, chitotriose and chitobiose. May participate in the defense against nematodes and other pathogens. Isoform 3 has no enzymatic activity.
Gene Name:
CHIT1
Uniprot ID:
Q13231
Molecular weight:
Not Available
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q2VT96
Molecular weight:
46615.5
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q1M0P3
Molecular weight:
33762.3
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q1M0P4
Molecular weight:
33747.3
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
CHIA
Uniprot ID:
A5D6V7
Molecular weight:
44306.1
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
CHIA
Uniprot ID:
Q5VUV5
Molecular weight:
45461.2