You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 23:22:27 UTC
Update Date2019-07-23 05:45:49 UTC
HMDB IDHMDB0003539
Secondary Accession Numbers
  • HMDB03539
Metabolite Identification
Common NameLevan
DescriptionLevan is a substantial component of bacterial plaque produced by certain streptococci and actinomyces, and lipopolysaccharides from Gram-negative bacteria. These bacterial products are B cell mitogens which may have an adjuvant or tolerizing effect on immune responses. (PubMed ID 346320 ).
Structure
Data?1563860749
Synonyms
ValueSource
(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
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 Solubility311 g/LALOGPS
logP-2.9ALOGPS
logP-6.3ChemAxon
logS-0.21ALOGPS
pKa (Strongest Acidic)10.23ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity101.84 m³·mol⁻¹ChemAxon
Polarizability47.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-6240900000-f1c5bb82595b7adde7a0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0159-4403119000-0804d302073c73682666JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-2689750000-eb151ecc90899c68eb42JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0709000000-943bc21e712c718fe599JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uec-4920000000-89d6f0013703f6c7c921JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-3904110000-2e605b3697e7dbace613JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ta-0900100000-3bc5ee3e1276649fddf1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-6900000000-d203a8851f7ebaeeb171JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Gum
  • Pancreas
  • Teeth
  • Tongue
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
FoodDB IDFDB023192
KNApSAcK IDNot Available
Chemspider ID17216231
KEGG Compound IDC01355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevan
METLIN ID6945
PubChem Compound22833608
PDB IDNot Available
ChEBI IDNot Available
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 ]