You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Amylose (HMDB0003403)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 20:13:38 UTC
Update Date2020-02-26 21:24:34 UTC
HMDB IDHMDB0003403
Secondary Accession Numbers
  • HMDB03403
Metabolite Identification
Common NameAmylose
DescriptionAmylose 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 ).
Structure
Data?1582752274
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1,4-alpha-D-Glucosyl)NHMDB
(1,4-alpha-D-Glucosyl)n+1HMDB
(1,4-alpha-D-Glucosyl)N-1HMDB
(1,4-alpha-delta-Glucosyl)NHMDB
(1,4-alpha-delta-Glucosyl)n+1HMDB
(1,4-alpha-delta-Glucosyl)N-1HMDB
1,4-alpha-D-GlucanHMDB
1,4-alpha-delta-GlucanHMDB
4-{(1,4)-alpha-D-glucosyl}(N-1)-D-glucoseHMDB
4-{(1,4)-alpha-delta-glucosyl}(N-1)-delta-glucoseHMDB
Amylose chainHMDB
a-D-MannoseHMDB
Α-D-mannoseHMDB
Chemical Formula(C12H20O11)nC2H6
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number9005-82-7
SMILES
CO[C@H]1O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
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 KeyPTHCMJGKKRQCBF-OLYDTGNASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logS-0.04ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9i-3329000000-2b7bd69033e8a4fea64aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-5eb2b079a3b131ab742eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fb9-9700000000-8631a9ae75f1a201adc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-9b80204fe6afbb2eaf15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-865ff3c21e042be41194Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-1900000000-ff3096b7f2c9d1141b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-c4b6f8b4217029a276d9Spectrum
MSMass Spectrum (Electron Ionization)splash10-0229-9000000000-3cd18e57966112492f50Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDFDB001130
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00718
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmylose
METLIN ID6917
PubChem Compound53477771
PDB IDNot Available
ChEBI ID28102
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceBreitinger, 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 ]
  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 ]
  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 ]
  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 ]
  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 ]

Enzymes

Enzyme Details
1. Glycogen debranching enzyme
General function:
Involved in catalytic activity
Specific function:
Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
Gene Name:
AGL
Uniprot ID:
P35573
Molecular weight:
Not Available
Enzyme Details
2. Glycogen phosphorylase, liver form
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
Enzyme Details
3. Glycogen phosphorylase, muscle form
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355
Enzyme Details
4. Glycogen phosphorylase, brain form
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
Enzyme Details
5. Glycogen [starch] synthase, liver
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS2
Uniprot ID:
P54840
Molecular weight:
80988.42
Enzyme Details
6. Glycogen [starch] synthase, muscle
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS1
Uniprot ID:
P13807
Molecular weight:
76482.48
Enzyme Details
7. Glucan , branching enzyme 1 variant
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q59ET0
Molecular weight:
86112.7