Carlinoside (CHEM023822)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:18:53 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023822
Identification
Common NameCarlinoside
ClassSmall Molecule
DescriptionA C-glycosyl compound that is luteolin substituted at positions 8 and 6 by alpha-L-arabinopyranosyl and beta-D-glucosyl residues respectively.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-C-beta-D-Glucosyl-8-C-alpha-L-arabinopyranosylluteolinChEBI
8-C-alpha-L-Arabinopyranosyl-6-C-beta-D-glucosylluteolinChEBI
Luteolin 6-C-beta-D-glucopyranoside-8-C-alpha-L-arabinopyranosideChEBI
Luteolin 6-C-glucoside-8-C-arabinosideChEBI
6-C-b-D-Glucosyl-8-C-a-L-arabinopyranosylluteolinGenerator
6-C-Β-D-glucosyl-8-C-α-L-arabinopyranosylluteolinGenerator
8-C-a-L-Arabinopyranosyl-6-C-b-D-glucosylluteolinGenerator
8-C-Α-L-arabinopyranosyl-6-C-β-D-glucosylluteolinGenerator
Luteolin 6-C-b-D-glucopyranoside-8-C-a-L-arabinopyranosideGenerator
Luteolin 6-C-β-D-glucopyranoside-8-C-α-L-arabinopyranosideGenerator
Chemical FormulaC26H28O15
Average Molecular Mass580.492 g/mol
Monoisotopic Mass580.143 g/mol
CAS Registry Number59952-97-5
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]-4H-chromen-4-one
Traditional Namecarlinoside
SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C([C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C26H28O15/c27-5-13-18(33)21(36)23(38)26(41-13)15-19(34)14-10(30)4-12(7-1-2-8(28)9(29)3-7)40-24(14)16(20(15)35)25-22(37)17(32)11(31)6-39-25/h1-4,11,13,17-18,21-23,25-29,31-38H,5-6H2/t11-,13+,17-,18+,21-,22+,23+,25-,26-/m0/s1
InChI KeyXBGYTZHKGMCEGE-VYUBKLCTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.23 g/LALOGPS
logP-0.75ALOGPS
logP-2.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area267.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity135.17 m³·mol⁻¹ChemAxon
Polarizability55.36 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0000190000-2450d43c11e4848e4340Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1500490000-5680c8c8b3f03115406aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07bs-2105950000-c07dcc5f25c44a73419dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1000390000-149494eabad65b3bcfbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08or-6301790000-46605de8614708adc728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9102410000-ad51de8420121e5237b8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB001558
Phenol Explorer IDNot Available
KNApSAcK IDC00006184
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID3421
PubChem Compound ID442584
Kegg Compound IDC10026
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10820082
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17981413
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21801714
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=905416