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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:22:27 UTC
Update Date2021-09-14 15:44:38 UTC
HMDB IDHMDB0003539
Secondary Accession Numbers
  • HMDB03539
Metabolite Identification
Common NameLevan
DescriptionLevan, also known as polyfructose, 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. Levan has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make levan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Levan.
Structure
Thumb
Synonyms
ValueSource
PolyfructoseMeSH
(2,6-beta-D-Fructosyl)NHMDB
(2,6-beta-D-Fructosyl)n+1HMDB
(2,6-beta-delta-Fructosyl)NHMDB
(2,6-beta-delta-Fructosyl)n+1HMDB
2,6-beta-D-FructanHMDB
2,6-beta-delta-FructanHMDB
FructanHMDB
Levan NHMDB
Chemical FormulaC18H32O16
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
IUPAC Name(2R,3S,4S,5S)-5-{[(2S,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]methoxy}-2-(hydroxymethyl)oxolane-2,3,4-triol
Traditional Namefructans
CAS Registry Number9013-95-0
SMILES
OC[C@H]1O[C@@](CO)(OC[C@H]2O[C@@](CO)(CO[C@H]3O[C@](O)(CO)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O16/c19-1-7-9(23)14(28)18(5-22,33-7)31-2-8-10(24)12(26)16(3-20,32-8)6-30-15-11(25)13(27)17(29,4-21)34-15/h7-15,19-29H,1-6H2/t7-,8-,9-,10-,11+,12+,13+,14+,15+,16+,17-,18-/m1/s1
InChI KeyAIHDCSAXVMAMJH-GFBKWZILSA-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
  • C-glycosyl compound
  • Disaccharide
  • O-glycosyl compound
  • Ketal
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Dialkyl ether
  • Acetal
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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 Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Pancreas
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023192
KNApSAcK IDC00001647
Chemspider ID17216231
KEGG Compound IDC01355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevan
METLIN ID6945
PubChem Compound22833608
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDLEVAN1000
MarkerDB IDNot Available
Good Scents IDrw1653871
References
Synthesis ReferencePark, Hae-Eun; Park, Na Hee; Kim, Min-Jeong; Lee, Tae Ho; Lee, Hyeon Gyu; Yang, Ji-Young; Cha, Jaeho. Enzymatic synthesis of fructosyl oligosaccharides by levansucrase from Microbacterium laevaniformans ATCC 15953. Enzyme and Microbial Technology (2003), 32(7) p.820-827
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kleessen B, Elsayed NA, Loehren U, Schroedl W, Krueger M: Jerusalem artichokes stimulate growth of broiler chickens and protect them against endotoxins and potential cecal pathogens. J Food Prot. 2003 Nov;66(11):2171-5. [PubMed:14627303 ]