Record Information
Version1.0
Creation date2011-09-21 00:25:26 UTC
Update date2015-10-09 22:32:18 UTC
Primary IDFDB023154
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number1398-61-4
Structure
Thumb
Synonyms
SynonymSource
beta-1,4-Poly-N-acetyl-D-glucosamineHMDB
beta-1,4-Poly-N-acetyl-delta-glucosamineHMDB
Poly 2-acetamido-2-deoxy-D-glucoseHMDB
Poly 2-acetamido-2-deoxy-delta-glucoseHMDB
[1,4-(N-Acetyl-beta-D-glucosaminyl)]NHMDB
[1,4-(N-Acetyl-beta-D-glucosaminyl)]n+1HMDB
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]NHMDB
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]n+1HMDB
[1,4-(N-Acetyl-beta-D-glucosaminyl)]nhmdb
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]nhmdb
Poly 2-Acetamido-2-deoxy-D-glucosehmdb
Poly 2-Acetamido-2-deoxy-delta-glucosehmdb
Predicted Properties
PropertyValueSource
Water Solubility3.17 g/LALOGPS
logP-2ALOGPS
logP-7.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area295.29 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity153.69 m³·mol⁻¹ChemAxon
Polarizability68.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H49N3O16
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
InChI IdentifierInChI=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 KeyDJHJJVWPFGHIPH-OODMECLYSA-N
Isomeric SMILESCC(=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
Average Molecular Weight683.6992
Monoisotopic Molecular Weight683.311282535
Classification
DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uka-2152319000-658fce771663f92f0a2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ba-0010109000-89428956b30f72897007JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-0010209000-d06ed3801f5ec6d32d09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9633418000-4c5b1141f3376b47f49dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010095000-8a3e26b84405429fddfaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h90-2222139000-0f3e2e92e577e9a7d4d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9503011000-aeecf620c6bc4822954eJSpectraViewer
ChemSpider ID399508
ChEMBL IDNot Available
KEGG Compound IDC00461
Pubchem Compound ID21252321
Pubchem Substance IDNot Available
ChEBI ID17029
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03362
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2242111
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChitin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
N-acetyl-D-glucosamine kinaseNAGKQ9UJ70
Acidic mammalian chitinaseCHIAQ9BZP6
Chitotriosidase-1CHIT1Q13231
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Glutamate MetabolismSMP00072 map00250
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference