ECMDB: Dextrin (ECMDB21651) (M2MDB002045)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (346)

Record Information

Version

2.0

Creation Date

2012-08-15 08:51:32 -0600

Update Date

2015-09-17 15:41:21 -0600

Secondary Accession Numbers

ECMDB21651

Identification

Name:

Dextrin

Description

Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch or glycogen. Dextrins are mixtures of polymers of D-glucose units linked by -(1_4) or -(1_6) glycosidic bonds. The cyclical dextrins are known as cyclodextrins. They are formed by enzymatic degradation of starch by certain bacteria, for example, Bacillus macerans. Cyclodextrins have toroidal structures formed by 6-8 glucose residues. (Wikipedia) In E. coli metabolism, the enzyme alpha-amylase (EC 3.2.1.1) catalyzes the breakdown of glycogen into dextrin. (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

British gum
Caloreen
Corn dextrin
Crystal gum
Dextrid
Dextrina Bianca
Dextrine
Dextrins
Fortodex

Chemical Formula:

C₁₈H₃₂O₁₆

Weight:

Average: 504.4371
Monoisotopic: 504.169034976

InChI Key:

FYGDTMLNYKFZSV-MRCIVHHJSA-N

InChI:

InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16+,17?,18?/m1/s1

CAS number:

9004-53-9

IUPAC Name:

2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional IUPAC Name:

amylose

SMILES:

OC[C@H]1OC(O[C@H]2[C@H](O)[C@@H](O)C(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a trisaccharide (MALTOTRIOSE )
a linear malto-oligosaccharide (MALTOTRIOSE )
a short glucan (MALTOTRIOSE )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	554 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-6.5	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	47.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Starch + Water <> Dextrin + Starch
Glycogen + Phosphate > Alpha-D-glucose 1-phosphate + Dextrin + Dextrin
Dextrin + Water + Dextrin > debranched limit dextrin + Maltotetraose

SMPDB Pathways:

Starch and sucrose metabolism

PW000941

KEGG Pathways:

Starch and sucrose metabolism ec00500

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-2321900000-2c06af6e8c61473ee773	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-001r-4112149000-cef7720a9158e02f2779	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_46) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_27) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_121) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_122) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_124) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_125) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_126) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_266) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_19) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_40) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_55) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_65) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_75) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_76) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_77) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_131) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_133) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_211) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_213) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_214) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_215) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_218) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_219) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06vu-0509620000-d5199f4e8a350b10f5a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0809100000-9bba0a873c235685e755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-1912000000-47259f8b59f9be52f363	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06vu-0509620000-d5199f4e8a350b10f5a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0809100000-9bba0a873c235685e755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-1912000000-47259f8b59f9be52f363	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06vu-0509620000-d5199f4e8a350b10f5a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0809100000-9bba0a873c235685e755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-1912000000-47259f8b59f9be52f363	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0536960000-0aea29e0372e2dfb2ff8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bi-2925300000-fdb113a75d83b27864c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3921000000-8faa9fe46329a3130ea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0536960000-0aea29e0372e2dfb2ff8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bi-2925300000-fdb113a75d83b27864c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3921000000-8faa9fe46329a3130ea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0536960000-0aea29e0372e2dfb2ff8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bi-2925300000-fdb113a75d83b27864c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3921000000-8faa9fe46329a3130ea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0201490000-5516cf65275ea8244c0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bvs-1607930000-133513553ba8d0cecb5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bd-9310100000-5740681ad309d019462d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1002980000-d8f6dba60506c768fd51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pba-9315740000-73a320207e66cfc146e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a70-9633100000-824013b286e00d77f08c	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB06857
Pubchem Compound ID	62698
Kegg ID	C00721
ChemSpider ID	848
Wikipedia	Dextrin
BioCyc ID	Not Available

Enzymes

Protein Details

1. Glycogen phosphorylase

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:: glgP
Uniprot ID:: P0AC86
Molecular weight:: 93172

Reactions

(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.

Protein Details

2. Alpha-amylase

General function:: Involved in catalytic activity
Specific function:: Since only maltooligosaccharides up to a chain length of 6 glucose units are actively transported through the cytoplasmic membrane via the membrane-bound complex of three proteins, malF, malG, and malK, longer maltooligosaccharides must first be degraded by the periplasmic alpha-amylase, the malS protein
Gene Name:: malS
Uniprot ID:: P25718
Molecular weight:: 75712

Reactions

Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units.

Protein Details

3. Cytoplasmic alpha-amylase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in oligosaccharides and polysaccharides
Gene Name:: amyA
Uniprot ID:: P26612
Molecular weight:: 56639

Reactions

Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units.

Protein Details

4. Glycogen debranching enzyme

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the alpha-1,6-glucosidic linkages in glycogen which has first been partially depolymerized by phosphorylase. Shows only very little activity with native glycogen
Gene Name:: glgX
Uniprot ID:: P15067
Molecular weight:: 73576

Dextrin (ECMDB21651) (M2MDB002045)

Structure for #<Compound:0xa5b2d3ec>

Enzymes

Reactions

Reactions

Reactions