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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-03-03 11:46:32 UTC
Update Date2021-09-14 15:44:43 UTC
HMDB IDHMDB0011742
Secondary Accession Numbers
  • HMDB11742
Metabolite Identification
Common NameKojibiose
DescriptionKojibiose is a disaccharide. It can be found in honey, koji extract, sweet potato starch, sake and beer, and also in polysaccharides and sugar chains of glycoproteins. There are many methods of preparation including the isolation of a partial acetolyzate of dextran from Leuconostoc mecenteroides. However a more effective method with high efficiency was achieved using kojibiose phosphorylase with D-glucose and beta-D-glucose-1-phosphate as substrates. Kojibiose was also found as one of the components of glucose caramel, following thermal degradation.
Structure
Thumb
Synonyms
ValueSource
2-alpha-D-Glucosyl-D-glucoseChEBI
2-O-alpha-D-Glucopyranosyl-D-glucoseChEBI
2-a-D-Glucosyl-D-glucoseGenerator
2-Α-D-glucosyl-D-glucoseGenerator
2-O-a-D-Glucopyranosyl-D-glucoseGenerator
2-O-Α-D-glucopyranosyl-D-glucoseGenerator
alpha-D-Glucopyranosyl-(1->2)-D-glucoseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanal
Traditional Namekojibiose
CAS Registry Number2140-29-6
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=O
InChI Identifier
InChI=1S/C12H22O11/c13-1-4(16)7(17)8(18)5(2-14)22-12-11(21)10(20)9(19)6(3-15)23-12/h2,4-13,15-21H,1,3H2/t4-,5+,6-,7-,8-,9-,10+,11-,12+/m1/s1
InChI KeyPZDOWFGHCNHPQD-OQPGPFOOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Beta-hydroxy aldehyde
  • Oxane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aldehyde
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001143
KNApSAcK IDC00050477
Chemspider ID144601
KEGG Compound IDC19632
BioCyc IDALPHA-KOJIBIOSE
BiGG IDNot Available
Wikipedia LinkKojibiose
METLIN IDNot Available
PubChem Compound164939
PDB IDNot Available
ChEBI ID33020
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.