Bovine Metabolome Database: Showing metabocard for Chitosan (BMDB0003404)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:04:17 UTC

Update Date

2020-05-11 20:49:15 UTC

BMDB ID

BMDB0003404

Secondary Accession Numbers

BMDB03404

Metabolite Identification

Common Name

Chitosan

Description

Chitosan, also known as chicol or chitopearl 3510, 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. Based on a literature review a significant number of articles have been published on Chitosan.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-1,4-Poly-D-glucosamine	HMDB
beta-1,4-Poly-delta-glucosamine	HMDB
Chicol	HMDB
Chitopearl 3510	HMDB
Chitopearl BC 3000	HMDB
Chitopearl BCW 2500	HMDB
Chitopearl BCW 3000	HMDB
Chitopearl BCW 3500	HMDB
Chitopearl BCW 3505	HMDB
Chitopearl BCW 3507	HMDB
CTA 4	HMDB
Deacetylchitin	HMDB
Flonac C	HMDB
Flonac N	HMDB
Kimitsu chitosan F	HMDB
Kimitsu chitosan F 2	HMDB
Kimitsu chitosan H	HMDB
Kimitsu chitosan L	HMDB
Kimitsu chitosan m	HMDB
Kytex H	HMDB
Kytex m	HMDB
Poliglusam	HMDB
Sea cure F	HMDB
Sea cure plus	HMDB
YEA	HMDB
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]methoxycarboximidate	HMDB
Chitosan	MeSH

Chemical Formula

C₅₆H₁₀₃N₉O₃₉

Average Molecular Weight

1526.4539

Monoisotopic Molecular Weight

1525.635314599

IUPAC Name

methyl 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 Name

chitosan

CAS Registry Number

9012-76-4

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 Key

FLASNYPZGWUPSU-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

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
logP	-2.6	ALOGPS
logP	-18	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	8	ChemAxon
Hydrogen Acceptor Count	46	ChemAxon
Hydrogen Donor Count	29	ChemAxon
Polar Surface Area	808 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	321.21 m³·mol⁻¹	ChemAxon
Polarizability	144.92 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0101090000-0af9d88d6e547a866bbb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-2505390220-902ec8da722e5ec5abbc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1606390000-b1593d4ad805f4f2e702	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0r6r-4181970430-07dfcf890d2963fd841d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1436891112-9f1d5fc3dc6dc10242dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1340910000-8954a5bf7dad983817a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-1001950000-68536e28102cb2056d7d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-5102691011-e76175d3f0bcd34f3a96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i0-5719756223-7bd4cf98b39884bfd043	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08ov-0904241110-9d44fc210009a1c3ab6e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ml-0901030100-fb92df4c6000e4bcb3f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dm-3901010000-2ba9b0e887f4ac55c9cf	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Bladder
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Platelet
Prostate Tissue

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003404

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015634

KNApSAcK ID

Not Available

Chemspider ID

64870

KEGG Compound ID

C00734

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chitosan

METLIN ID

Not Available

PubChem Compound

71853

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Chitosan (BMDB0003404)

Structure for BMDB0003404 (Chitosan)