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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-30 12:41:45 UTC
Update Date2021-09-14 15:46:12 UTC
HMDB IDHMDB0006698
Secondary Accession Numbers
  • HMDB06698
Metabolite Identification
Common NameTri-N-acetylchitotriose
DescriptionTri-N-acetylchitotriose belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. Tri-N-acetylchitotriose has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make tri-N-acetylchitotriose a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Tri-N-acetylchitotriose.
Structure
Thumb
Synonyms
ValueSource
(g1CNAC)3HMDB
N,N',n''-triacetyl chitotrioseHMDB
N,N',n''-triacetylchitintrioseHMDB
N,N',n''-triacetylchitotrioseHMDB
N-AcetylchitotrioseHMDB
Tri(N-acetyl-D-glucosamine)HMDB
Tris(N-acetylglucosamine)HMDB
TriGlcNAcMeSH, HMDB
Tri-glcnacMeSH, HMDB
O-2-acetamido-2-Deoxy-beta-D-glucopyranosyl-(1-4)-O-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-4)-2-acetamido-2-deoxy-D-glucopyranoseMeSH, HMDB
N,N',n''- triacetyl chitotrioseMeSH, HMDB
N-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]ethanimidateGenerator, HMDB
Chemical FormulaC24H41N3O16
Average Molecular Weight627.5928
Monoisotopic Molecular Weight627.248682279
IUPAC NameN-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4S,5R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
CAS Registry Number38864-21-0
SMILES
CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H](O)[C@H]1NC(C)=O)[C@H](O)CO
InChI Identifier
InChI=1S/C24H41N3O16/c1-8(32)25-11(4-28)17(36)21(12(35)5-29)42-24-16(27-10(3)34)20(39)22(14(7-31)41-24)43-23-15(26-9(2)33)19(38)18(37)13(6-30)40-23/h4,11-24,29-31,35-39H,5-7H2,1-3H3,(H,25,32)(H,26,33)(H,27,34)/t11-,12+,13+,14+,15+,16+,17+,18+,19+,20+,21+,22+,23-,24-/m0/s1
InChI KeyLRDDKCYRFNJZBX-WHFMPQCRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy aldehyde
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Aldehyde
  • Organonitrogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point304 - 306 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB024030
KNApSAcK IDNot Available
Chemspider ID110328
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123774
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSingh, Suddham; Packwood, John; Samuel, Christopher J.; Critchley, P.; Crout, David H. G. Glycosidase-catalyzed oligosaccharide synthesis: preparation of N-acetylchito-oligosaccharides using the b-N-acetylhexosaminidase of Aspergillus oryzae. Carbohydrate Research (1995), 279 293-305.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prieels JP, Dolmans M, Schindler M, Sharon N: The binding of glycoconjugates to human-milk D-galactosyltransferase. Eur J Biochem. 1976 Jul 15;66(3):579-82. [PubMed:821753 ]
  2. Silano M, De Vincenzi M: Bioactive antinutritional peptides derived from cereal prolamins: a review. Nahrung. 1999 Jun;43(3):175-84. [PubMed:10399351 ]