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Record Information
Creation Date2006-08-12 19:21:29 UTC
Update Date2013-02-09 00:12:29 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameChitin
DescriptionChitin is an unusual substance as it is a naturally occurring polymer. Its breakdown is conducted by bacteria which have receptors to simple sugars from the decomposition of chitin. If chitin is detected they then produce enzymes to digest the chitin by reducing it to simple sugars and ammonia. Chitin (IPA: [Kaitin]) is one of the main components in the cell walls of fungi, the exoskeletons of insects and other arthropods, and in some other animals. It is a polysaccharide; it is constructed from units of acetylglucosamine (more completely, N-acetyl-D-glucos-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. A linear polysaccharide of beta-1->4 linked units of acetylglucosamine. It is the second most abundant biopolymer on earth, found especially in insects and fungi. When deacetylated it is called chitosan.
  1. beta-1,4-Poly-N-acetyl-D-glucosamine
  2. beta-1,4-Poly-N-acetyl-delta-glucosamine
  3. Poly 2-Acetamido-2-deoxy-D-glucose
  4. Poly 2-Acetamido-2-deoxy-delta-glucose
  5. [1,4-(N-Acetyl-beta-D-glucosaminyl)]N
  6. [1,4-(N-Acetyl-beta-D-glucosaminyl)]N+1
  7. [1,4-(N-Acetyl-beta-delta-glucosaminyl)]N
  8. [1,4-(N-Acetyl-beta-delta-glucosaminyl)]N+1
Chemical FormulaC28H49N3O16
Average Molecular Weight683.6992
Monoisotopic Molecular Weight683.311282535
IUPAC NameN-[(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 NameN-[(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
CAS Registry Number1398-61-4
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
  • Glucosamine
  • Amino sugar
  • Glycosyl compound
  • C-glycosyl compound
  • Oxane
  • Monosaccharide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
StatusExpected but not Quantified
  • Endogenous
  • Component of Aminosugars metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility31.0 mg/mLALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area295.29 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity153.69 m3·mol-1ChemAxon
Polarizability68.75 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014051z000-89428956b30f72897007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017073z000-d06ed3801f5ec6d32d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-zpfeh6x000-4c5b1141f3376b47f49dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-20423zm000-8a3e26b84405429fddfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-ab7a5cz000-0f3e2e92e577e9a7d4d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-zm2d256000-aeecf620c6bc4822954eView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Spleen
  • Testes
Amino Sugar MetabolismSMP00045map00520
Glutamate MetabolismSMP00072map00250
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023154
KNApSAcK IDNot Available
Chemspider ID399508
KEGG Compound IDC00461
BiGG ID2242111
Wikipedia LinkChitin
NuGOwiki LinkHMDB03362
Metagene LinkHMDB03362
PubChem Compound21252321
PDB IDNot Available
ChEBI ID17029
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)Download (PDF)
General References
  1. Gheri G, Sgambati E, Thyrion GD, Vichi D, Orlandini GE: The oligosaccharidic content of the glycoconjugates of the prepubertal descended and undescended testis: lectin histochemical study. Ital J Anat Embryol. 2004 Apr-Jun;109(2):69-84. [15481156 ]
  2. Hatcher VB, Schwarzmann GO, Jeanloz RW, McArthur JW: Changes in the sialic acid concentration in the major cervical glycoprotein from the bonnet monkey (Macaca radiata) during a hormonally induced cycle. Fertil Steril. 1977 Jun;28(6):682-8. [405259 ]
  3. Collard CD, Montalto MC, Reenstra WR, Buras JA, Stahl GL: Endothelial oxidative stress activates the lectin complement pathway: role of cytokeratin 1. Am J Pathol. 2001 Sep;159(3):1045-54. [11549596 ]
  4. Nakajima M, Atsumi K, Kifune K, Miura K, Kanamaru H: Chitin is an effective material for sutures. Jpn J Surg. 1986 Nov;16(6):418-24. [3820865 ]
  5. Soule JB, Halverson AL, Becker RB, Pistole MC, Orenstein JM: A patient with acquired immunodeficiency syndrome and untreated Encephalitozoon (Septata) intestinalis microsporidiosis leading to small bowel perforation. Response to albendazole. Arch Pathol Lab Med. 1997 Aug;121(8):880-7. [9278619 ]
  6. Piskun RP, Pentiuk AA, Serkova VK, Polesia TL, Savitskaia EA: [Enterosorbents in the treatment of atherosclerosis] Eksp Klin Farmakol. 1998 Mar-Apr;61(2):69-74. [9621181 ]
  7. Kawashita M, Nakao M, Minoda M, Kim HM, Beppu T, Miyamoto T, Kokubo T, Nakamura T: Apatite-forming ability of carboxyl group-containing polymer gels in a simulated body fluid. Biomaterials. 2003 Jun;24(14):2477-84. [12695074 ]
  8. Howling GI, Dettmar PW, Goddard PA, Hampson FC, Dornish M, Wood EJ: The effect of chitin and chitosan on the proliferation of human skin fibroblasts and keratinocytes in vitro. Biomaterials. 2001 Nov;22(22):2959-66. [11575470 ]
  9. Vasstrand EN, Jensen HB: Affinity chromatography of human saliva lysozyme and effect of pH and ionic strength on lytic activity. Scand J Dent Res. 1980 Jun;88(3):219-28. [6932088 ]
  10. Shibuya N, Nakamura K, Ogoshi K, Ohta T, Hori Y, Kodama K, Yamamoto M: Modification of mutagenic activities of pro-mutagens by glyco-ursodeoxycholic acid in the Ames assay. Tohoku J Exp Med. 1999 Sep;189(1):1-9. [10622203 ]
  11. Ishihara C, Yoshimatsu K, Tsuji M, Arikawa J, Saiki I, Tokura S, Azuma I: Anti-viral activity of sulfated chitin derivatives against Friend murine leukaemia and herpes simplex type-1 viruses. Vaccine. 1993;11(6):670-4. [8391740 ]
  12. Zampini M, Pruzzo C, Bondre VP, Tarsi R, Cosmo M, Bacciaglia A, Chhabra A, Srivastava R, Srivastava BS: Vibrio cholerae persistence in aquatic environments and colonization of intestinal cells: involvement of a common adhesion mechanism. FEMS Microbiol Lett. 2005 Mar 15;244(2):267-73. [15766778 ]
  13. Xu Y, Olman V, Xu D: Clustering gene expression data using a graph-theoretic approach: an application of minimum spanning trees. Bioinformatics. 2002 Apr;18(4):536-45. [12016051 ]
  14. Sharaev PN, Strelkov NS, Sannikova AA, Zvorykin IA, Men'shikova NN, Sakhabutdinova EP, Gabdrakhmanova NK: [The method for detection of urinary lysozyme] Klin Lab Diagn. 2001 Apr;(4):52-3. [11393034 ]
  15. Farnia P, Mohammadi F, Zarifi Z, Tabatabee DJ, Ganavi J, Ghazisaeedi K, Farnia PK, Gheydi M, Bahadori M, Masjedi MR, Velayati AA: Improving sensitivity of direct microscopy for detection of acid-fast bacilli in sputum: use of chitin in mucus digestion. J Clin Microbiol. 2002 Feb;40(2):508-11. [11825964 ]
  16. Sano H, Matsukubo T, Shibasaki K, Itoi H, Takaesu Y: Inhibition of adsorption of oral streptococci to saliva treated hydroxyapatite by chitin derivatives. Bull Tokyo Dent Coll. 1991 Feb;32(1):9-17. [1668072 ]
  17. Johnson SM, Pappagianis D: The coccidioidal complement fixation and immunodiffusion-complement fixation antigen is a chitinase. Infect Immun. 1992 Jul;60(7):2588-92. [1612728 ]


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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
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:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Molecular weight:
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Molecular weight:
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Molecular weight:
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in chitin binding
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight: