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Human Metabolome Database Version 3.5

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Showing metabocard for Chitin (HMDB03362)

Record Information
Version 3.5
Creation Date 2006-08-12 13:21:29 -0600
Update Date 2013-02-08 17:12:29 -0700
HMDB ID HMDB03362
Secondary Accession Numbers None
Metabolite Identification
Common Name Chitin
Description Chitin 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  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 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 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
CAS Registry Number 1398-61-4
SMILES CC(=O)NC1[C@H](O)OC(CO)[C@@H](COC[C@@H]2OC(CO)[C@@H](COC[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3NC(C)=O)[C@H](O)C2NC(C)=O)[C@@H]1O
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
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Trisaccharides
Sub Class Trihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Dialkyl Ether
  • Glucosamine
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Trihexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 31 g/L ALOGPS
LogP -3.03 ALOGPS
LogP -7.9 ChemAxon
LogS -1.34 ALOGPS
pKa (strongest acidic) 11.57 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 16 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 295.29 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 153.69 ChemAxon
Polarizability 68.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
  • Intestine
  • Testes
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Glutamate Metabolism SMP00072 map00250 Link_out
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023154
KNApSAcK ID Not Available
Chemspider ID 399508 Link_out
KEGG Compound ID C00461 Link_out
BioCyc ID 14-N-ACETYL-BETA-D-GLUCOSAMINYLN1 Link_out
BiGG ID 2242111 Link_out
Wikipedia Link Chitin Link_out
NuGOwiki Link HMDB03362 Link_out
Metagene Link HMDB03362 Link_out
METLIN ID 6903 Link_out
PubChem Compound 21252321 Link_out
PDB ID Not Available
ChEBI ID 17029 Link_out
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.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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. Pubmed: 3820865 Link_out
  2. 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. Pubmed: 9278619 Link_out
  3. 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. Pubmed: 15481156 Link_out
  4. 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. Pubmed: 405259 Link_out
  5. 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. Pubmed: 9621181 Link_out
  6. 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. Pubmed: 12695074 Link_out
  7. 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. Pubmed: 11575470 Link_out
  8. 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. Pubmed: 6932088 Link_out
  9. 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. Pubmed: 11549596 Link_out
  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. Pubmed: 10622203 Link_out
  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. Pubmed: 8391740 Link_out
  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. Pubmed: 15766778 Link_out
  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. Pubmed: 12016051 Link_out
  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. Pubmed: 11393034 Link_out
  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. Pubmed: 11825964 Link_out
  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. Pubmed: 1668072 Link_out
  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. Pubmed: 1612728 Link_out
Enzymes
Name: N-acetyl-D-glucosamine kinase
Reactions:
  • ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 6-phosphate [RN:R01201]
Gene Name: NAGK
Uniprot ID: Q9UJ70 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acidic mammalian chitinase
Reactions:
  • Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins ALL_REAC (other) R01206 R02334 R06081(G) R06082(G) INHIBITOR Allosamidine [CPD:C05346]
Gene Name: CHIA
Uniprot ID: Q9BZP6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Chitotriosidase-1
Reactions:
  • Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins ALL_REAC (other) R01206 R02334 R06081(G) R06082(G) INHIBITOR Allosamidine [CPD:C05346]
Gene Name: CHIT1
Uniprot ID: Q13231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Chitinase family protein 3
Reactions:
    Gene Name: Not Available
    Uniprot ID: Q2VT96 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Chitinase family protein V2
    Reactions:
      Gene Name: Not Available
      Uniprot ID: Q1M0P3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Chitinase family protein V1
      Reactions:
        Gene Name: Not Available
        Uniprot ID: Q1M0P4 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: CHIA protein
        Reactions:
          Gene Name: CHIA
          Uniprot ID: A5D6V7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Chitinase, acidic
          Reactions:
            Gene Name: CHIA
            Uniprot ID: Q5VUV5 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA