Human Metabolome Database: Showing metabocard for Isomaltose (HMDB02923)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

3.6

Creation Date

2006-05-22 15:12:19 UTC

Update Date

2016-02-11 01:05:52 UTC

HMDB ID

HMDB02923

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isomaltose

Description

Isomaltose is a naturally occurring disaccharide composed of two glucose units in an alpha (1-6) glycosidic linkage. -- Pubchem. A deficiency of sucrase-isomaltase, an integral protein of the small intestine brush-border membrane responsible for catalyzing the hydrolysis of dietary sucrose and some of the products of starch digestion, results in osmotic diarrhea when the disaccharide is ingested, because absorption cannot occur until after hydrolysis produces the component monosaccharides. (OMIM 222800 ,). It is particularly suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions. --Wikipedia.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(GLC)2	ChEBI
6-O-alpha-D-Glucopyranosyl-D-glucopyranose	ChEBI
alpha-D-GLC-(1->6)-D-GLC	ChEBI
alpha-D-GLCP-(1->6)-D-GLCP	ChEBI
alpha-D-Glucosyl-(1->6)-D-glucose	ChEBI
Brachiose	ChEBI
Hunterioside	ChEBI
6-O-a-D-Glucopyranosyl-D-glucopyranose	Generator
6-O-α-D-glucopyranosyl-D-glucopyranose	Generator
a-D-GLC-(1->6)-D-GLC	Generator
α-D-GLC-(1->6)-D-GLC	Generator
a-D-GLCP-(1->6)-D-GLCP	Generator
α-D-GLCP-(1->6)-D-GLCP	Generator
a-D-Glucosyl-(1->6)-D-glucose	Generator
α-D-glucosyl-(1->6)-D-glucose	Generator
6-O-a-D-Glucopyranosyl-D-glucose	HMDB
6-O-alpha-D-Glucopyranosyl-D-glucose	HMDB
6-O-alpha-delta-Glucopyranosyl-delta-glucose	HMDB

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

IUPAC Name

(3R,4S,5S,6R)-6-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol

Traditional Name

brachiose

CAS Registry Number

499-40-1

SMILES

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

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11?,12+/m1/s1

InChI Key

InChIKey=DLRVVLDZNNYCBX-RTPHMHGBSA-N

Chemical Taxonomy

Description

This compound 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.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Polyol
Hemiacetal
1,2-diol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycosylglucose (CHEBI:28189 )
Disaccharides (C00252 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm (predicted from logP)

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
Water Solubility	511.0 mg/mL	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.17	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol^-1	ChemAxon
Polarizability	31.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ox-1709000000-e1aedea040f248898825	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9501000000-dfecff3e8858cc005d12	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-1e5c79ae513f06c8d563	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biofluid Locations

Blood
Saliva

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	68.98 +/- 24.26 uM	Adult (>18 years old)	Both	Kidney disease	10649708	details

Associated Disorders and Diseases

Disease References

Kidney disease
Burke RA, Moberly JB, Patel H, Shockley TR, Martis L: Maltose and isomaltose in uremic plasma following icodextrin administration. Adv Perit Dial. 1998;14:120-3. [10649708 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28189

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kuriyama M, Hiwatari R, Osame M, Igata A: Leucocyte alpha-1,4- and alpha-1,6-glucosidase activities towards oligosaccharides in late onset glycogenosis type II. Tohoku J Exp Med. 1990 Aug;161(4):343-51. [2256108 ]
Guddat S, Thevis M, Schanzer W: Identification and quantification of the plasma volume expander dextran in human urine by liquid chromatography-tandem mass spectrometry of enzymatically derived isomaltose. Biomed Chromatogr. 2005 Dec;19(10):743-50. [15856492 ]
Vitek V, Vitek K: Chromatography of sugars in body fluids. IV. Separation of isomaltose and lactose in urine by paper chromatography. Biochem Med. 1973 Feb;7(1):119-27. [4684081 ]

Enzymes

Enzyme Details

1. Sucrase-isomaltase, intestinal

General function:: Involved in catalytic activity
Specific function:: Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:: SI
Uniprot ID:: P14410
Molecular weight:: Not Available

Reactions

Isomaltose + Water → Alpha-D-Glucose + D-Glucose	details

Showing metabocard for Isomaltose (HMDB02923)

Structure for HMDB02923 (Isomaltose)

Enzymes

Reactions