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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
SynonymSource
Hesperetin 7-O-neohesperidosideHMDB
NeohesperidinHMDB
Hesperetin 7-neohesperidosidedb_source
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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.08%; H 5.61%; O 39.31%DFC
Melting PointMp 244°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -100 (c, 0.5 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Antitumor promoter35610 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.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— 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).