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Isorhoifolin (FDB016371)

Record Information
Version1.0
Creation date2010-04-08 22:12:24 UTC
Update date2019-11-26 03:13:08 UTC
Primary IDFDB016371
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsorhoifolin
DescriptionIsorhoifolin belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Isorhoifolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Isorhoifolin is found, on average, in the highest concentration within peppermints and olives. Isorhoifolin has also been detected, but not quantified in, several different foods, such as citrus, dills, orange mints, lemons, and german camomiles. This could make isorhoifolin a potential biomarker for the consumption of these foods.
CAS Number552-57-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.91 g/LALOGPS
logP0ALOGPS
logP-0.29ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity135.93 m³·mol⁻¹ChemAxon
Polarizability56.71 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O14
IUPAC name5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-8,10,18,20-29,31-36H,9H2,1H3
InChI KeyFKIYLTVJPDLUDL-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight578.5187
Monoisotopic Molecular Weight578.163555668
Classification
Description Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent5-O-methylated flavonoids
Alternative Parents
Substituents
  • 5-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous ester
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.06%; H 5.23%; O 38.72%DFC
Melting PointMp 269-270°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -98.2 (c, 1.19 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsorhoifolin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08g0-6491080000-c720cf0ac806590395f3Spectrum
Predicted GC-MSIsorhoifolin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-8376109000-5a6058e4871fec027dcaSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090040000-98b6a76703dc72bb1de52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-36a2014246a42fb91bf12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-4fa2544a4ecf6257b8462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-9b3a96dd95e5ea53a50e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-a0659bb16f6a1d30cf8b2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190170000-e6a011b2c517b66148ae2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0190100000-0ac27246c573953093cb2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1390000000-c60cce4351b700be4d542016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-4480390000-8a21a3d04d43f8c6ecef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2490010000-60dbb4223bc5556618ab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2290000000-b364b0d0e8048c0d9bb52016-08-03View Spectrum
NMRNot Available
ChemSpider ID4526806
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5377847
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID233
DrugBank IDNot Available
HMDB IDHMDB37349
CRC / DFC (Dictionary of Food Compounds) IDKQW27-E:KQW47-K
EAFUS IDNot Available
Dr. Duke IDAPIGENIN-7-O-RUTINOSIDE|ISORHOIFOLIN
BIGG IDNot Available
KNApSAcK IDC00004156
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
anti complementaryDUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.