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Record Information
Version4.0
Creation Date2006-05-22 15:12:19 UTC
Update Date2017-10-23 19:04:01 UTC
HMDB IDHMDB0002923
Secondary Accession Numbers
  • HMDB02923
Metabolite Identification
Common NameIsomaltose
DescriptionIsomaltose 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
Thumb
Synonyms
ValueSource
(GLC)2ChEBI
6-O-alpha-D-Glucopyranosyl-D-glucopyranoseChEBI
alpha-D-GLC-(1->6)-D-GLCChEBI
alpha-D-GLCP-(1->6)-D-GLCPChEBI
alpha-D-Glucosyl-(1->6)-D-glucoseChEBI
BrachioseChEBI
HunteriosideChEBI
6-O-a-D-Glucopyranosyl-D-glucopyranoseGenerator
6-O-α-D-glucopyranosyl-D-glucopyranoseGenerator
a-D-GLC-(1->6)-D-GLCGenerator
α-D-GLC-(1->6)-D-GLCGenerator
a-D-GLCP-(1->6)-D-GLCPGenerator
α-D-GLCP-(1->6)-D-GLCPGenerator
a-D-Glucosyl-(1->6)-D-glucoseGenerator
α-D-glucosyl-(1->6)-D-glucoseGenerator
6-O-a-D-Glucopyranosyl-D-glucoseHMDB
6-O-alpha-D-Glucopyranosyl-D-glucoseHMDB
6-O-alpha-delta-Glucopyranosyl-delta-glucoseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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 Namebrachiose
CAS Registry Number499-40-1
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 KeyDLRVVLDZNNYCBX-RTPHMHGBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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 Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

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
Polarizability31.22 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0iu0-2695000000-b644ad8ee930f0244c0fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-4236229000-cc57f0250001605061e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-1709000000-e1aedea040f248898825View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9501000000-dfecff3e8858cc005d12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-1e5c79ae513f06c8d563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0219000000-77abf6de9ff79d4ddfcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fs-2915000000-70455c0b7e9dbd96c5b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ikd-6930000000-6466a054f554b370d893View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3559000000-3d5899762c5229ad1bd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-4933000000-db46210de280609b14c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9520000000-c953abfa4f36a9b0b9e1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified68.98 +/- 24.26 uMAdult (>18 years old)Both
Kidney disease
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001220
KNApSAcK IDC00018660
Chemspider ID388333
KEGG Compound IDC00252
BioCyc IDCPD-1243
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID412
PubChem Compound439193
PDB IDNot Available
ChEBI ID28189
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  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