Human Metabolome Database Version 3.5

Showing metabocard for Amylose (HMDB03403)

Record Information
Version 3.5
Creation Date 2006-08-12 14:13:38 -0600
Update Date 2013-05-29 13:38:10 -0600
HMDB ID HMDB03403
Secondary Accession Numbers None
Metabolite Identification
Common Name Amylose
Description Amylose is defined as a linear molecule of (1→4) linked alpha-D-glucopyranosyl units, but it is today well established that some molecules are slightly branched by (1→6)-alpha-linkages. The oldest criteria for linearity consisted in the susceptibility of the molecule to complete hydrolysis by beta-amylase. This enzyme splits the (1→4) bonds from the non-reducing end of a chain releasing beta-maltosyl units, but cannot cleave the (1→6) bonds. When degraded by pure beta-amylase, linear macromolecules are completely converted into maltose, whereas branched chains give also one beta-limit dextrin consisting of the remaining inner core polysaccharide structure with its outer chains recessed. Starches of different botanical origins possess different granular sizes, morphology, polymorphism and enzyme digestibility. These characteristics are related to the chemical structures of the amylopectin and amylose and how they are arranged in the starch granule. (PMID 9730163 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (1,4-alpha-D-Glucosyl)N
  2. (1,4-alpha-D-Glucosyl)N+1
  3. (1,4-alpha-D-Glucosyl)N-1
  4. (1,4-alpha-delta-Glucosyl)N
  5. (1,4-alpha-delta-Glucosyl)N+1
  6. (1,4-alpha-delta-Glucosyl)N-1
  7. 1,4-alpha-D-Glucan
  8. 1,4-alpha-delta-Glucan
  9. 4-{(1,4)-alpha-D-Glucosyl}(N-1)-D-glucose
  10. 4-{(1,4)-alpha-delta-Glucosyl}(N-1)-delta-glucose
  11. Amylose
  12. Amylose chain
Chemical Formula Not Available
Average Molecular Weight Not Available
Monoisotopic Molecular Weight Not Available
IUPAC Name Not Available
Traditional IUPAC Name Not Available
CAS Registry Number 9005-82-7
SMILES Not Available
InChI Identifier InChI=1S/C14H26O11/c1-21-11-5(3-15)24-14(10(20)7(11)17)25-12-6(4-16)23-13(22-2)9(19)8(12)18/h5-20H,3-4H2,1-2H3/t5-,6-,7-,8-,9-,10-,11-,12-,13+,14-/m1/s1
InChI Key PTHCMJGKKRQCBF-OLYDTGNASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Disaccharides
Sub Class Dihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Dialkyl Ether
  • Glycosyl Compound
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Dihexoses
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 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
Formal Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001130
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C00718 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Amylose Link_out
NuGOwiki Link HMDB03403 Link_out
Metagene Link HMDB03403 Link_out
METLIN ID 6917 Link_out
PubChem Compound 53477771 Link_out
PDB ID Not Available
ChEBI ID 28102 Link_out
References
Synthesis Reference Breitinger, Hans-Georg. Synthesis and characterization of 2,3-di-O-alkylated amyloses: Hydrophobic substitution destabilizes helical conformation. Biopolymers (2003), 69(3), 301-310.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Topping DL, Gooden JM, Brown IL, Biebrick DA, McGrath L, Trimble RP, Choct M, Illman RJ: A high amylose (amylomaize) starch raises proximal large bowel starch and increases colon length in pigs. J Nutr. 1997 Apr;127(4):615-22. Pubmed: 9109613 Link_out
  2. Klein B, Foreman JA: Amylolysis of a chromogenic substrate, Cibachron Blue F3GA-amylose: kinetics and mechanism. Clin Chem. 1980 Feb;26(2):250-3. Pubmed: 6153298 Link_out
  3. Langkilde AM, Ekwall H, Bjorck I, Asp NG, Andersson H: Retrograded high-amylose corn starch reduces cholic acid excretion from the small bowel in ileostomy subjects. Eur J Clin Nutr. 1998 Nov;52(11):790-5. Pubmed: 9846590 Link_out
  4. Traub WH: Studies on neutralization of human serum bactericidal activity by sodium amylosulfate. J Clin Microbiol. 1977 Aug;6(2):128-31. Pubmed: 330560 Link_out
  5. Buleon A, Colonna P, Planchot V, Ball S: Starch granules: structure and biosynthesis. Int J Biol Macromol. 1998 Aug;23(2):85-112. Pubmed: 9730163 Link_out

Enzymes
Name: Glycogen debranching enzyme
Reactions: Not Available
Gene Name: AGL
Uniprot ID: P35573 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, liver form
Reactions: Not Available
Gene Name: PYGL
Uniprot ID: P06737 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, muscle form
Reactions: Not Available
Gene Name: PYGM
Uniprot ID: P11217 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen phosphorylase, brain form
Reactions: Not Available
Gene Name: PYGB
Uniprot ID: P11216 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase, liver
Reactions: Not Available
Gene Name: GYS2
Uniprot ID: P54840 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase, muscle
Reactions: Not Available
Gene Name: GYS1
Uniprot ID: P13807 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucan , branching enzyme 1 variant
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: Q59ET0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA