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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:19 UTC
Update Date2019-07-23 05:45:38 UTC
HMDB IDHMDB0002923
Secondary Accession Numbers
  • HMDB02923
Metabolite Identification
Common NameIsomaltose
DescriptionIsomaltose (CAS: 499-40-1) 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 favourable in products for diabetics and prediabetic dispositions (Wikipedia).
Structure
Data?1563860738
Synonyms
ValueSource
6-O-alpha-D-Glucopyranosyl-D-glucoseHMDB
6-O-alpha-D-Glucopyranosyl-beta-D-glucopyranoseHMDB
6-O-Α-D-glucopyranosyl-D-glucoseHMDB
6-O-Α-D-glucopyranosyl-β-D-glucopyranoseHMDB
D-IsomaltoseHMDB
beta-D-IsomaltoseHMDB
beta-IsomaltoseHMDB
Β-D-isomaltoseHMDB
Β-isomaltoseHMDB
IsomaltoseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2R,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(2R,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
CAS Registry Number37169-69-0
SMILES
OC[C@H]1O[C@H](OC[C@H]2O[C@@H](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 KeyDLRVVLDZNNYCBX-BTLHAWITSA-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
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility511 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.17ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0wmi-1962000000-d9a6a2ac051471ab8d06Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0w29-1952000000-2b5f1147c92a3429ee12Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-1709000000-e1aedea040f248898825Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9501000000-dfecff3e8858cc005d12Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-1e5c79ae513f06c8d563Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified68.98 +/- 24.26 uMAdult (>18 years old)Both
Kidney disease
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. 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. [PubMed:10649708 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsomaltose
METLIN IDNot Available
PubChem Compound10357
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDISOMAL
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:15856492 ]
  2. 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. [PubMed:2256108 ]
  3. 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. [PubMed:4684081 ]

Enzymes

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-Glucosedetails