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Showing Compound Hesperetin 7-neohesperidoside (FDB002679)

Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2019-11-26 02:57:48 UTC
Primary IDFDB002679
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHesperetin 7-neohesperidoside
DescriptionHesperetin 7-neohesperidoside belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. Hesperetin 7-neohesperidoside is found, on average, in the highest concentration within a few different foods, such as grapefruits (Citrus X paradisi), grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima), and lemons (Citrus limon) and in a lower concentration in sweet oranges (Citrus sinensis). Hesperetin 7-neohesperidoside has also been detected, but not quantified in, several different foods, such as citrus, limes (Citrus aurantiifolia), mandarin orange (clementine, tangerine), and pummelos (Citrus maxima). This could make hesperetin 7-neohesperidoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hesperetin 7-neohesperidoside.
CAS Number13241-33-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility3.37 g/LALOGPS
logP-0.27ALOGPS
logP-0.31ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity140.77 m³·mol⁻¹ChemAxon
Polarizability60.79 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H34O15
IUPAC name7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3
InChI KeyARGKVCXINMKCAZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(OC3OC(CO)C(O)C(O)C3OC3OC(C)C(O)C(O)C3O)C=C2O1
Average Molecular Weight610.5606
Monoisotopic Molecular Weight610.189770418
Classification
Description Belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassCyclobutane lignans
Sub ClassNot Available
Direct ParentCyclobutane lignans
Alternative Parents
Substituents
  • Cyclobutane lignan skeleton
  • Dibenzylbutane lignan skeleton
  • Stilbene
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHesperetin 7-neohesperidoside, non-derivatized, GC-MS Spectrumsplash10-014j-0930000000-e06187b94b91bece73ebSpectrum
GC-MSHesperetin 7-neohesperidoside, non-derivatized, GC-MS Spectrumsplash10-014j-0930000000-e06187b94b91bece73ebSpectrum
Predicted GC-MSHesperetin 7-neohesperidoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0595-7211090000-ad27da094f49ce125ea4Spectrum
Predicted GC-MSHesperetin 7-neohesperidoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0lk9-9311018000-7c8542e0ec6068c1b53eSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000009000-22f8094c7ada8928b6942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0003009000-68522ebdb396405fee532017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0000009000-04cc3791b0a80ce12a352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009001000-a784d35122c71c756b902017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000009000-f7ccd876e0275858b7842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-19148a209130a5aa898c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0439501000-9b8f76f75a3bb45c37942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w29-0961000000-70b0466bf27ab8ba54602021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-8d4547c9300481f47b642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w29-0961000000-f28f6c5de90993cbc0172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000009000-3c9b3e61420c62c3ef5e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-0000009000-5389085d4e4a4c9388322021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0009000000-560c9f79f2b1714bb14a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0pb9-0006009000-84cd0bf5ac7208a8b6db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0439501000-3bd1a33265783be93f7b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w29-0960000000-a8efbff7c5c9972af64c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0pb9-0017009000-97193b5009abc913a2dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0pb9-0017009000-de07800bc91724543b912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0pb9-0006009000-de6a04d7ce700b9463a82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0337932000-4f816481d88bc4dc284a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0469400000-61a492d660c6ac50cab22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1945000000-a59da63ead1fe09512142015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r01-4639756000-940018a6761f4084c98a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2a-2947520000-9e4e51caf6c79a3d2ddc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9757000000-cad4fecc590b2576b2fb2015-04-25View Spectrum
NMRNot Available
ChemSpider ID203119
ChEMBL IDNot Available
KEGG Compound IDC09806
Pubchem Compound ID232990
Pubchem Substance IDNot Available
ChEBI ID59016
Phenol-Explorer ID211
DrugBank IDNot Available
HMDB IDHMDB30748
CRC / DFC (Dictionary of Food Compounds) IDCNB06-R:CNB11-P
EAFUS IDNot Available
Dr. Duke IDNEOHESPERIDIN
BIGG IDNot Available
KNApSAcK IDC00000987
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 ID211
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).