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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-03 10:06:33 UTC
Update Date2017-12-07 02:32:20 UTC
HMDB IDHMDB0011730
Secondary Accession Numbers
  • HMDB11730
Metabolite Identification
Common NameMelezitose
DescriptionMelezitose, also spelled melicitose, is a nonreducing trisaccharide sugar that is produced by many plant sap eating insects, including aphids such as Cinara pilicornis by an enzyme reaction. This is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees. This is useful to the lice as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the latter of which is an isomer of sucrose (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
MelizitoseChEBI
O-alpha-D-Glucopyranosyl-(1-3)-beta-D-fructofuranosyl-alpha-D-glucopyranosideChEBI
O-a-D-Glucopyranosyl-(1-3)-b-D-fructofuranosyl-a-D-glucopyranosideGenerator
O-α-D-glucopyranosyl-(1-3)-β-D-fructofuranosyl-α-D-glucopyranosideGenerator
D-(+)-MelezitoseHMDB
D-MelezitoseHMDB
MelicitoseHMDB
O alpha-D-Glucopyranosyl-(1,3)-O beta-D-fructofuranosyl-(2,1) alpha-D-glucopyranosideMeSH
Chemical FormulaC18H32O16
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namemelezitose
CAS Registry Number597-12-6
SMILES
OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1
InChI KeyQWIZNVHXZXRPDR-WSCXOGSTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility781 g/LALOGPS
logP-3.3ALOGPS
logP-6.3ChemAxon
logS0.19ALOGPS
pKa (Strongest Acidic)11.86ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.19 m³·mol⁻¹ChemAxon
Polarizability46.29 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0i00-1953000000-152bbb0aef234498930eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmi-0942000000-7e0c4e11c584463d3f19View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-024r-1111900000-729d3332348e9c16c80aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ls-2622139000-19f0f16d5a87e6037f2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0509000000-2dd0b195efbe7e5f8d20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-0903000000-2b951d98f0e95e8c119eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1901000000-b6cfc2f98d768add98a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-1369110000-0f63a9c90d4056cc3d28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ml-0609000000-d6ac63b4b4d93616ddf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3913000000-922e484d08c61f224f57View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Prostate Tissue
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>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
FoodDB IDFDB001203
KNApSAcK IDC00001141
Chemspider ID83787
KEGG Compound IDC08243
BioCyc IDCPD-13409
BiGG IDNot Available
Wikipedia LinkMelezitose
METLIN IDNot Available
PubChem Compound92817
PDB IDNot Available
ChEBI ID6731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available