Showing Compound Card for Cynaroside (CDB000340)

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Record Information
Version1.0
Created at2020-03-19 00:31:50 UTC
Updated at2020-11-18 16:35:04 UTC
CannabisDB IDCDB000340
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCynaroside
DescriptionLuteolin-7-O-glucoside, also known as 7-O-glucoluteolin or cinaroside, belongs to the class of organic compounds known as flavonoid O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. glucoside. Because of the conjugation of glucose, Luteolin 7-O-glucoside is a moderately water-soluble compound. Luteolin 7-O-glucoside is found, on average, in a few different plants, spices and foods, such as Mexican oregano, anises, and wild celeries and in a lower concentration in lentils, and wild carrots. common buckwheats, corns, globe artichokes, roman camomiles, and orange mints. Luteolin 7-O-glucoside is one of veral dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranosideChEBI
2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-oneChEBI
7-GlucoluteolinChEBI
7-GlucosylluteolinChEBI
7-O-beta-D-Glucosyl-5,7,3',4'-tetrahydroxyflavoneChEBI
CinarosideChEBI
CynarosideChEBI
Luteolin 7-monoglucosideChEBI
Luteolin 7-O-glucopyranosideChEBI
Luteolin 7-O-glucosideChEBI
Luteolin-7-glucosideChEBI
LuteolosideChEBI
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl b-D-glucopyranosideGenerator
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranosideGenerator
2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-oneGenerator
7-O-b-D-Glucosyl-5,7,3',4'-tetrahydroxyflavoneGenerator
7-O-Β-D-glucosyl-5,7,3',4'-tetrahydroxyflavoneGenerator
Luteolin 7-glucosideChEBI
DaphneflavonolosideHMDB
FlavopurposideHMDB
GlucoluteolinHMDB
Luteolin 7-O-beta-D-glucosideHMDB
Luteolin 7-O-b-D-glucosideGenerator
Luteolin 7-O-β-D-glucosideGenerator
NephrocizinMeSH
Luteolin-7-O-monoglucosideMeSH
Luteolin-7-O-beta-D-glucopyranosideMeSH
Luteolin-7-beta-D-glucosideMeSH
3',4',5,7-Tetrahydroxyflavone 7-beta-D-glucopyranosidePhytoBank
3',4',5,7-Tetrahydroxyflavone 7-β-D-glucopyranosidePhytoBank
3’,4’,5,7-Tetrahydroxyflavone 7-β-D-glucopyranosidePhytoBank
3',4',5-Trihydroxyflavone 7-O-beta-D-glucopyranosidePhytoBank
3',4',5-Trihydroxyflavone 7-O-β-D-glucopyranosidePhytoBank
3’,4’,5-Trihydroxyflavone 7-O-β-D-glucopyranosidePhytoBank
7-(beta-D-Glucosyloxy)-3',4',5-trihydroxyflavonePhytoBank
7-(β-D-Glucosyloxy)-3',4',5-trihydroxyflavonePhytoBank
7-(β-D-Glucosyloxy)-3’,4’,5-trihydroxyflavonePhytoBank
7-O-beta-D-GlucosylluteolinPhytoBank
7-O-β-D-GlucosylluteolinPhytoBank
Luteolin 7-O-beta-D-glucopyranosidePhytoBank
Luteolin 7-O-β-D-glucopyranosidePhytoBank
Luteolin 7-O-beta-glucopyranosidePhytoBank
Luteolin 7-O-β-glucopyranosidePhytoBank
Luteolin 7-O-beta-glucosidePhytoBank
Luteolin 7-O-β-glucosidePhytoBank
Luteolin 7-beta-D-glucosidePhytoBank
Luteolin 7-β-D-glucosidePhytoBank
Chemical FormulaC21H20O11
Average Molecular Weight448.38
Monoisotopic Molecular Weight448.1006
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameluteolin 7-O-glucoside
CAS Registry Number5373-11-5
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyPEFNSGRTCBGNAN-QNDFHXLGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.58ALOGPS
logP0.14ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.04 m³·mol⁻¹ChemAxon
Polarizability42.98 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCynaroside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001r-8934600000-7e7c6044b90fb9c11463Spectrum
Predicted GC-MSCynaroside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f72-4730119000-f82ba729f371b8abdbdaSpectrum
Predicted GC-MSCynaroside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0010900030-c10d893db863fa97d0a82017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0010900030-c10d893db863fa97d0a82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0090000000-f076599705f9f223d3602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-000i-0090100000-fe6850abbcec4fe56dd92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0012-0190500000-bcf45c556204b1713d582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0030900020-65868b413ea8969c46722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0019-0090000000-0908e4e690a4acb6edfc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-f15806fb1fd62f75af542017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001a-0190400000-862638c136c541fb742b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0091000000-f63c0d3cebcf6fc2e5072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-0040900000-e3f9043e8fac7872cb662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-1ff8e42522b8a1f6961a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-cb0df3f467ea51e6ab182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000j-0090600000-8f1dad507334d836e2a82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0190000000-e3aa1461dda1c7043d2d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-000i-0090000000-31bb8bd03bfd2eff538b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0091100000-ea4c2b653cea6f4747662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0090000000-8392154e4309f46037d52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0019-0090000000-a15f658ade963370f0c32021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190600000-49dfd37238ba14bc6c112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0190000000-8733c538660a8dd11d052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1390000000-ceeece13914238abed462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-1261900000-e1ec4112e692ec8fbbd62016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1190100000-bcbf2a30e128889e80472016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2190000000-954ea2eef82d3bedfb362016-08-04View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035588
DrugBank IDNot Available
Phenol Explorer Compound ID245
FoodDB IDFDB014280
KNApSAcK IDC00004266
Chemspider ID4444241
KEGG Compound IDC03951
BioCyc IDLUTEOLIN-7-O-BETA-D-GLUCOSIDE
BiGG IDNot Available
Wikipedia LinkCynaroside
METLIN IDNot Available
PubChem Compound5280637
PDB IDNot Available
ChEBI ID27994
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]