Record Information
Version1.0
Creation date2010-04-08 22:13:37 UTC
Update date2019-11-26 03:15:58 UTC
Primary IDFDB018285
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRhoifolin
DescriptionRhoifolin, also known as rhoifoloside, 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. Rhoifolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Rhoifolin is found, on average, in the highest concentration within grapefruit/pummelo hybrids. Rhoifolin has also been detected, but not quantified in, several different foods, such as wild rices, barley, lemons, citrus, and oats. This could make rhoifolin a potential biomarker for the consumption of these foods.
CAS Number17306-46-6
Structure
Thumb
Synonyms
SynonymSource
(-)-RhoifolinHMDB
Apigenin 7-neohesperidosideHMDB
Apigenin 7-O-neohesperidosideHMDB
RhoifolosideHMDB
Rhoifolindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.55 g/LALOGPS
logP0ALOGPS
logP-0.29ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity135.93 m³·mol⁻¹ChemAxon
Polarizability57.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O14
IUPAC name7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3
InChI KeyRPMNUQRUHXIGHK-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight578.5187
Monoisotopic Molecular Weight578.163555668
Classification
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
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • Disaccharide
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.06%; H 5.23%; O 38.72%DFC
Melting PointMp 251-253°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]29D -110 (c, 0.21 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRhoifolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-044j-9521280000-0917f10a5b6baacf6838Spectrum
Predicted GC-MSRhoifolin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-008i-9302015000-6ef91fbe8aa7e8fc76c2Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-ecaa3a6967cd09282dc3Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0000090000-ae30f112a923d142978dSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0000090000-501b2152bc23d443237eSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0090020000-497da5597601c9bf0733Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-af8a381295c4517905c6Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0000090000-1af95f29bd8c772c698fSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-016r-0090060000-65ee1d530eaa66fb9956Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-70638c60bb73139ff045Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00or-0090080000-ca27dac15acc1f6d0074Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-a82fc388c680ba729a9aSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0090000000-3d077aa0ecfce0b2de45Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0190000000-b5a5f9125b955aef70a2Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-016r-0090060000-e22c953df117ba9a83f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290750000-ae5f87d4e475bdc0d5c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190300000-9106eeed3bb3b73c3d3aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1390100000-a988cf269c380e5007c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07xr-3582980000-51841a3f9c22e8835c6fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2591310000-52c1352d6ec17fe1b727Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6590000000-b1a49bd18b6cdc7767d5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000190000-48e73583084c06ab4561Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pi-0050790000-9b843f6502778be0c2e7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090010000-76c066300921436abb72Spectrum
NMRNot Available
ChemSpider ID4573039
ChEMBL IDNot Available
KEGG Compound IDC12627
Pubchem Compound ID5459217
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID235
DrugBank IDNot Available
HMDB IDHMDB38848
CRC / DFC (Dictionary of Food Compounds) IDCNR54-G:LHZ94-L
EAFUS IDNot Available
Dr. Duke IDRHOIFOLIN|APIGENIN-7-O-NEOHESPEROSIDE
BIGG IDNot Available
KNApSAcK IDC00004157
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.