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Human Metabolome Database Version 3.5

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Showing metabocard for Tri-N-acetylchitotriose (HMDB06698)

Record Information
Version 3.5
Creation Date 2007-05-30 06:41:45 -0600
Update Date 2013-02-08 17:15:10 -0700
HMDB ID HMDB06698
Secondary Accession Numbers None
Metabolite Identification
Common Name Tri-N-acetylchitotriose
Description Tri-N-acetylchitotriose is an oligosaccharide that may prevent the action of certain prolamins (antinutritional peptides) from some cereals (e. g. wheat, barley, and rye) that adversely affect in vivo the intestinal mucosa of coeliac patients. (PMID: 10399351 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (G1cNAC)3
  2. N,N',N''-Triacetyl chitotriose
  3. N,N',N''-Triacetylchitintriose
  4. N,N',N''-Triacetylchitotriose
  5. N-Acetylchitotriose
  6. Tri(N-acetyl-D-glucosamine)
  7. Tris(N-acetylglucosamine)
Chemical Formula C24H41N3O16
Average Molecular Weight 627.5928
Monoisotopic Molecular Weight 627.248682279
IUPAC Name N-[(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 IUPAC Name N-[(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 Number 38864-21-0
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 Key LRDDKCYRFNJZBX-WHFMPQCRSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Trisaccharides
Sub Class Trihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Trihexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 304 - 306 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 57.8 g/L ALOGPS
LogP -2.43 ALOGPS
LogP -8 ChemAxon
LogS -1.04 ALOGPS
pKa (strongest acidic) 11.34 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Hydrogen Acceptor Count 16 ChemAxon
Hydrogen Donor Count 11 ChemAxon
Polar Surface Area 303.13 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 135.48 ChemAxon
Polarizability 59.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024030
KNApSAcK ID Not Available
Chemspider ID 110328 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06698 Link_out
Metagene Link HMDB06698 Link_out
METLIN ID Not Available
PubChem Compound 123774 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Singh, 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) Download (PDF)
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 Link_out