NEOHESPERIDIN DIHYDROCHALCONE (CHEM006867)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:18:40 UTC
Update Date2016-11-09 01:09:49 UTC
Accession NumberCHEM006867
Identification
Common NameNEOHESPERIDIN DIHYDROCHALCONE
ClassSmall Molecule
DescriptionA member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage. It is found in sweet orange.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Neohesperidine DCMeSH
Neohesperidine dihydrochalconeMeSH
Chemical FormulaC28H36O15
Average Molecular Mass612.581 g/mol
Monoisotopic Mass612.205 g/mol
CAS Registry Number20702-77-6
IUPAC Name1-(4-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,6-dihydroxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
Traditional Nameneohesperidin dihydrochalcone
SMILES[H][C@@]1(C)O[C@@]([H])(O[C@@]2([H])[C@]([H])(OC3=CC(O)=C(C(=O)CCC4=CC(O)=C(OC)C=C4)C(O)=C3)O[C@]([H])(CO)[C@@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O
InChI IdentifierInChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
InChI KeyITVGXXMINPYUHD-CUVHLRMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Nitrobenzene
  • Nitroaromatic compound
  • Benzoyl
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility2.04 g/LALOGPS
logP0.05ALOGPS
logP0.75ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.18 m³·mol⁻¹ChemAxon
Polarizability60.55 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 6V, Negativesplash10-0udi-0009001000-a784d35122c71c756b90Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0001009000-828aa8353246f5f4043dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0009103000-97bc3acb4370bf9313c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0w29-0119005000-c793e997a188821d0f59Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 42V, positivesplash10-0udi-0000960000-472e33b531c61b98300cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-0348932000-df6cd9b375db7056eae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0649400000-2a887032b44aa75c8d3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-0936000000-bd32f06b0c49d82b7fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-4529746000-3a493f7c0089f7f95e3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2j-2936510000-2937915e513b94cadbe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9758000000-8ebac12374f6c970b439Spectrum
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 IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNeohesperidin_dihydrochalcone
Chemspider IDNot Available
ChEBI ID83535
PubChem Compound ID30231
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23562496
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24274324
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24530446