Chitosan (CHEM030362)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:50:45 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030362
Identification
Common NameChitosan
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 FormulaC7H15NO4
Average Molecular Mass177.198 g/mol
Monoisotopic Mass177.100 g/mol
CAS Registry Number9012-76-4
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
SMILESCC1OC(CO)C(O)C(O)C1N
InChI IdentifierInChI=1S/C7H15NO4/c1-3-5(8)7(11)6(10)4(2-9)12-3/h3-7,9-11H,2,8H2,1H3
InChI KeyXJSPDRFMLGJORM-UHFFFAOYSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0101090000-0af9d88d6e547a866bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2505390220-902ec8da722e5ec5abbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1606390000-b1593d4ad805f4f2e702Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r6r-4181970430-07dfcf890d2963fd841dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1436891112-9f1d5fc3dc6dc10242ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1340910000-8954a5bf7dad983817a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-1001950000-68536e28102cb2056d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5102691011-e76175d3f0bcd34f3a96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-5719756223-7bd4cf98b39884bfd043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ov-0904241110-9d44fc210009a1c3ab6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ml-0901030100-fb92df4c6000e4bcb3f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-3901010000-2ba9b0e887f4ac55c9cfSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003404
FooDB IDFDB015634
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChitosan
Chemspider ID64870
ChEBI IDNot Available
PubChem Compound ID71853
Kegg Compound IDC00734
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rashad, 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.