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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:04:46 UTC
Update Date2019-07-23 06:30:01 UTC
HMDB IDHMDB0039576
Secondary Accession Numbers
  • HMDB39576
Metabolite Identification
Common NameLyciumoside II
DescriptionLyciumoside II is found in coffee and coffee products. Lyciumoside II is a constituent of Lycium chinense (Chinese boxthorn).
Structure
Data?1563863401
SynonymsNot Available
Chemical FormulaC38H64O17
Average Molecular Weight792.9046
Monoisotopic Molecular Weight792.414350622
IUPAC Name2-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,6Z,10E)-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraen-1-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,6Z,10E)-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraen-1-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number150396-01-3
SMILES
C\C(CC\C=C(/C)COC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)=C\CC\C(C)=C\CCC(C)(OC1OC(CO)C(O)C(O)C1O)C=C
InChI Identifier
InChI=1S/C38H64O17/c1-6-38(5,55-36-33(49)30(46)27(43)24(17-40)52-36)15-9-14-21(3)11-7-10-20(2)12-8-13-22(4)19-50-37-34(31(47)28(44)25(18-41)53-37)54-35-32(48)29(45)26(42)23(16-39)51-35/h6,10,13-14,23-37,39-49H,1,7-9,11-12,15-19H2,2-5H3/b20-10-,21-14+,22-13+
InChI KeyQAUYGCMOBFCRSP-AFAFYZGOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Diterpenoid
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Fatty acyl
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP0.22ALOGPS
logP-0.63ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.85ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area277.91 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity196.83 m³·mol⁻¹ChemAxon
Polarizability84.01 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gi-0110609400-a0d94721bee325e8cff1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0232906000-3f250cd7e41679a116c3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-1422903200-0d10f22ca84ee332c6caJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0203-1401239700-c84bf927a931427567a2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1901317400-2adbd106653a81010933JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r0-4900332100-9fb81a8d95805f1e8cbbJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB019198
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.