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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 20:14:08 UTC
Update Date2021-09-14 15:46:45 UTC
HMDB IDHMDB0003404
Secondary Accession Numbers
  • HMDB03404
Metabolite Identification
Common NameChitosan
DescriptionChitosan 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
Data?1582752275
Synonyms
ValueSource
beta-1,4-Poly-D-glucosamineHMDB
beta-1,4-Poly-delta-glucosamineHMDB
ChicolHMDB
Chitopearl 3510HMDB
Chitopearl BC 3000HMDB
Chitopearl BCW 2500HMDB
Chitopearl BCW 3000HMDB
Chitopearl BCW 3500HMDB
Chitopearl BCW 3505HMDB
Chitopearl BCW 3507HMDB
CTA 4HMDB
DeacetylchitinHMDB
Flonac CHMDB
Flonac NHMDB
Kimitsu chitosan FHMDB
Kimitsu chitosan F 2HMDB
Kimitsu chitosan HHMDB
Kimitsu chitosan LHMDB
Kimitsu chitosan mHMDB
Kytex HHMDB
Kytex mHMDB
PoliglusamHMDB
Sea cure FHMDB
Sea cure plusHMDB
YEAHMDB
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]methoxycarboximidateHMDB
ChitosanMeSH
Chemical FormulaC56H103N9O39
Average Molecular Weight1526.4539
Monoisotopic Molecular Weight1525.635314599
IUPAC Namemethyl 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 Namechitosan
CAS Registry Number9012-76-4
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 KeyFLASNYPZGWUPSU-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility69.3 g/LALOGPS
logP-2.6ALOGPS
logP-18ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge8ChemAxon
Hydrogen Acceptor Count46ChemAxon
Hydrogen Donor Count29ChemAxon
Polar Surface Area808 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity321.21 m³·mol⁻¹ChemAxon
Polarizability144.92 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0101090000-0af9d88d6e547a866bbb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2505390220-902ec8da722e5ec5abbc2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1606390000-b1593d4ad805f4f2e7022017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r6r-4181970430-07dfcf890d2963fd841d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1436891112-9f1d5fc3dc6dc10242dd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1340910000-8954a5bf7dad983817a72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-1001950000-68536e28102cb2056d7d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5102691011-e76175d3f0bcd34f3a962021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-5719756223-7bd4cf98b39884bfd0432021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ov-0904241110-9d44fc210009a1c3ab6e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ml-0901030100-fb92df4c6000e4bcb3f52021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-3901010000-2ba9b0e887f4ac55c9cf2021-09-08View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000e-2412901011-b627de538bf19c98aa142021-09-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, H2O, predicted)Not Available2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Placenta
  • Platelet
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015634
KNApSAcK IDNot Available
Chemspider ID64870
KEGG Compound IDC00734
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChitosan
METLIN IDNot Available
PubChem Compound71853
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceRashad, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Stone CA, Wright H, Clarke T, Powell R, Devaraj VS: Healing at skin graft donor sites dressed with chitosan. Br J Plast Surg. 2000 Oct;53(7):601-6. [PubMed:11000077 ]
  2. van der Lubben IM, Verhoef JC, Borchard G, Junginger HE: Chitosan for mucosal vaccination. Adv Drug Deliv Rev. 2001 Nov 5;52(2):139-44. [PubMed:11718937 ]
  3. Rosales-Cortes M, Peregrina-Sandoval J, Banuelos-Pineda J, Castellanos-Martinez EE, Gomez-Pinedo UA, Albarran-Rodriguez E: [Regeneration of the axotomised sciatic nerve in dogs using the tubulisation technique with Chitosan biomaterial preloaded with progesterone]. Rev Neurol. 2003 Jun 16-30;36(12):1137-41. [PubMed:12833231 ]
  4. 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 ]
  5. Rana V, Babita K, Goyal D, Tiwary A: Sodium citrate cross-linked chitosan films: optimization as substitute for human/rat/rabbit epidermal sheets. J Pharm Pharm Sci. 2004 Dec 20;8(1):10-7. [PubMed:15946593 ]
  6. Pogozheva AV, Baigarin EK, Derbeneva SA, Varsanovich EA, Miagkova MA: [The study of influence of chitosan on clinical, metabolic and immune parameters in patients with cardiovascular diseases]. Vopr Pitan. 2005;74(4):27-30. [PubMed:16265912 ]
  7. Lin CW, Lin JC: Characterization and blood coagulation evaluation of the water-soluble chitooligosaccharides prepared by a facile fractionation method. Biomacromolecules. 2003 Nov-Dec;4(6):1691-7. [PubMed:14606897 ]
  8. Drenda P, Lampe P, Gorka Z, Bursig H, Dylag S: [Evaluation of the usefulness of dressings made from chitosan and lyophilized human placenta on wound healing]. Wiad Lek. 1997;50 Suppl 1 Pt 2:252-6. [PubMed:9424883 ]
  9. Guo JX, Ping QN, Dong J, Li ZR, Li CJ: [Mechanisms of action of transportation of liposomes and chitosan-coated liposomes containing leuprolide across intestine and Caco-2 cell]. Yao Xue Xue Bao. 2005 Jan;40(1):65-70. [PubMed:15881330 ]
  10. Zahorska-Markiewicz B, Krotkiewski M, Olszanecka-Glinianowicz M, Zurakowski A: [Effect of chitosan in complex management of obesity]. Pol Merkur Lekarski. 2002 Aug;13(74):129-32. [PubMed:12420344 ]
  11. Lekka M, Laidler P, Ignacak J, Labedz M, Lekki J, Struszczyk H, Stachura Z, Hrynkiewicz AZ: The effect of chitosan on stiffness and glycolytic activity of human bladder cells. Biochim Biophys Acta. 2001 Aug 22;1540(2):127-36. [PubMed:11513974 ]
  12. Saintigny G, Bonnard M, Damour O, Collombel C: Reconstruction of epidermis on a chitosan cross-linked collagen-GAG lattice: effect of fibroblasts. Acta Derm Venereol. 1993 Jun;73(3):175-80. [PubMed:8105612 ]
  13. Suzuki T, Mizushima Y, Umeda T, Ohashi R: Further biocompatibility testing of silica-chitosan complex membrane in the production of tissue plasminogen activator by epithelial and fibroblast cells. J Biosci Bioeng. 1999;88(2):194-9. [PubMed:16232597 ]
  14. Gingras M, Paradis I, Berthod F: Nerve regeneration in a collagen-chitosan tissue-engineered skin transplanted on nude mice. Biomaterials. 2003 Apr;24(9):1653-61. [PubMed:12559825 ]
  15. Springate CM, Jackson JK, Gleave ME, Burt HM: Efficacy of an intratumoral controlled release formulation of clusterin antisense oligonucleotide complexed with chitosan containing paclitaxel or docetaxel in prostate cancer xenograft models. Cancer Chemother Pharmacol. 2005 Sep;56(3):239-47. Epub 2005 Apr 30. [PubMed:15864591 ]