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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2021-10-13 04:40:19 UTC
HMDB IDHMDB0002927
Secondary Accession Numbers
  • HMDB02927
Metabolite Identification
Common NameNaringin
DescriptionNaringin, also known as naringoside or naringin hydrate, is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. Naringin belongs to the flavonoid family. Flavonoids consist of 15 carbon atoms in 3 rings, 2 of which must be benzene rings connected by a 3 carbon chain. Naringin contains the basic flavonoid structure along with one rhamnose and one glucose unit attached to its aglycone portion, called naringenin, at the 7-carbon position. The steric hindrance provided by the two sugar units makes naringin less potent than its aglycone counterpart, naringenin. Naringin is a bitter tasting compound. Naringin is found, on average, in the highest concentration within a few different foods, such as rosemaries, grapefruit/pummelo hybrids, and grapefruits and in a lower concentration in grape wines, pummelo, and beers. Naringin has also been detected, but not quantified in several different foods, such as citrus, limes, herbs and spices, common oregano, and mandarin orange (clementine, tangerine). Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.
Structure
Data?1582752259
Synonyms
ValueSource
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]ChEBI
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucosideChEBI
Naringenin 7-O-neohesperidosideChEBI
NaringosideChEBI
Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside]Generator
Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside]Generator
Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucosideGenerator
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucosideGenerator
4',5,7-Trihydroxyflavanone 7-rhamnoglucosideMeSH
CyclorelMeSH
AurantiinMeSH
Naringenin-7-hesperidosideMeSH
Naringin dihydrochalconeMeSH
Naringin sodiumMeSH
4'5-DiOH-flavone-7-rhglucHMDB
Naringin hydrateHMDB
NobiletinHMDB
Chemical FormulaC27H32O14
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
IUPAC Name(2S)-7-{[(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}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namenaringin
CAS Registry Number10236-47-2
SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C27H32O14/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/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChI KeyDFPMSGMNTNDNHN-ZPHOTFPESA-N
Chemical Taxonomy
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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling Point922.00 to 926.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1 mg/mL at 40 °CNot Available
LogP-0.44PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker217.32930932474
[M+H]+Baker240.6230932474
[M+H]+MetCCS_train_pos237.45330932474
[M-H]-Not Available217.329http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543
[M+H]+Not Available239.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000543
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.06 g/LALOGPS
logP10(-0.24) g/LALOGPS
logP10(-0.16) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.3 m³·mol⁻¹ChemAxon
Polarizability56.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaringinC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O5296.7Standard polar33892256
NaringinC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O4704.0Standard non polar33892256
NaringinC[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O5202.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naringin,1TMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4747.1Semi standard non polar33892256
Naringin,1TMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4757.2Semi standard non polar33892256
Naringin,1TMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4766.9Semi standard non polar33892256
Naringin,1TMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4762.6Semi standard non polar33892256
Naringin,1TMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4821.9Semi standard non polar33892256
Naringin,1TMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4754.3Semi standard non polar33892256
Naringin,1TMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4748.7Semi standard non polar33892256
Naringin,1TMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4772.6Semi standard non polar33892256
Naringin,2TMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4635.8Semi standard non polar33892256
Naringin,2TMS,isomer #10C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4667.1Semi standard non polar33892256
Naringin,2TMS,isomer #11C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4622.2Semi standard non polar33892256
Naringin,2TMS,isomer #12C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4611.0Semi standard non polar33892256
Naringin,2TMS,isomer #13C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4637.0Semi standard non polar33892256
Naringin,2TMS,isomer #14C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4665.3Semi standard non polar33892256
Naringin,2TMS,isomer #15C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4727.0Semi standard non polar33892256
Naringin,2TMS,isomer #16C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4644.9Semi standard non polar33892256
Naringin,2TMS,isomer #17C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4634.5Semi standard non polar33892256
Naringin,2TMS,isomer #18C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4662.4Semi standard non polar33892256
Naringin,2TMS,isomer #19C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4731.5Semi standard non polar33892256
Naringin,2TMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4699.8Semi standard non polar33892256
Naringin,2TMS,isomer #20C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4636.6Semi standard non polar33892256
Naringin,2TMS,isomer #21C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4627.9Semi standard non polar33892256
Naringin,2TMS,isomer #22C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4661.4Semi standard non polar33892256
Naringin,2TMS,isomer #23C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4709.2Semi standard non polar33892256
Naringin,2TMS,isomer #24C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4698.9Semi standard non polar33892256
Naringin,2TMS,isomer #25C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4726.8Semi standard non polar33892256
Naringin,2TMS,isomer #26C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4639.7Semi standard non polar33892256
Naringin,2TMS,isomer #27C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4638.0Semi standard non polar33892256
Naringin,2TMS,isomer #28C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4649.1Semi standard non polar33892256
Naringin,2TMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4635.7Semi standard non polar33892256
Naringin,2TMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4646.3Semi standard non polar33892256
Naringin,2TMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4620.5Semi standard non polar33892256
Naringin,2TMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4597.5Semi standard non polar33892256
Naringin,2TMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4624.5Semi standard non polar33892256
Naringin,2TMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4645.6Semi standard non polar33892256
Naringin,2TMS,isomer #9C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4708.4Semi standard non polar33892256
Naringin,3TMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4587.4Semi standard non polar33892256
Naringin,3TMS,isomer #10C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4556.9Semi standard non polar33892256
Naringin,3TMS,isomer #11C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4581.5Semi standard non polar33892256
Naringin,3TMS,isomer #12C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4590.8Semi standard non polar33892256
Naringin,3TMS,isomer #13C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4534.6Semi standard non polar33892256
Naringin,3TMS,isomer #14C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4510.4Semi standard non polar33892256
Naringin,3TMS,isomer #15C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4546.6Semi standard non polar33892256
Naringin,3TMS,isomer #16C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4537.5Semi standard non polar33892256
Naringin,3TMS,isomer #17C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4510.7Semi standard non polar33892256
Naringin,3TMS,isomer #18C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4546.1Semi standard non polar33892256
Naringin,3TMS,isomer #19C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4525.2Semi standard non polar33892256
Naringin,3TMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4545.1Semi standard non polar33892256
Naringin,3TMS,isomer #20C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4520.6Semi standard non polar33892256
Naringin,3TMS,isomer #21C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4522.7Semi standard non polar33892256
Naringin,3TMS,isomer #22C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4590.8Semi standard non polar33892256
Naringin,3TMS,isomer #23C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4567.9Semi standard non polar33892256
Naringin,3TMS,isomer #24C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4526.7Semi standard non polar33892256
Naringin,3TMS,isomer #25C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4511.9Semi standard non polar33892256
Naringin,3TMS,isomer #26C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4545.7Semi standard non polar33892256
Naringin,3TMS,isomer #27C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4620.3Semi standard non polar33892256
Naringin,3TMS,isomer #28C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4573.9Semi standard non polar33892256
Naringin,3TMS,isomer #29C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4564.8Semi standard non polar33892256
Naringin,3TMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4551.2Semi standard non polar33892256
Naringin,3TMS,isomer #30C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4589.2Semi standard non polar33892256
Naringin,3TMS,isomer #31C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4563.1Semi standard non polar33892256
Naringin,3TMS,isomer #32C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4544.9Semi standard non polar33892256
Naringin,3TMS,isomer #33C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4574.5Semi standard non polar33892256
Naringin,3TMS,isomer #34C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4527.1Semi standard non polar33892256
Naringin,3TMS,isomer #35C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4523.8Semi standard non polar33892256
Naringin,3TMS,isomer #36C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4527.3Semi standard non polar33892256
Naringin,3TMS,isomer #37C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4608.1Semi standard non polar33892256
Naringin,3TMS,isomer #38C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4552.3Semi standard non polar33892256
Naringin,3TMS,isomer #39C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4539.6Semi standard non polar33892256
Naringin,3TMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4527.8Semi standard non polar33892256
Naringin,3TMS,isomer #40C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4571.5Semi standard non polar33892256
Naringin,3TMS,isomer #41C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4591.0Semi standard non polar33892256
Naringin,3TMS,isomer #42C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4582.4Semi standard non polar33892256
Naringin,3TMS,isomer #43C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4608.4Semi standard non polar33892256
Naringin,3TMS,isomer #44C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4561.4Semi standard non polar33892256
Naringin,3TMS,isomer #45C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4558.0Semi standard non polar33892256
Naringin,3TMS,isomer #46C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4563.5Semi standard non polar33892256
Naringin,3TMS,isomer #47C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4596.1Semi standard non polar33892256
Naringin,3TMS,isomer #48C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4584.5Semi standard non polar33892256
Naringin,3TMS,isomer #49C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4610.0Semi standard non polar33892256
Naringin,3TMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4505.5Semi standard non polar33892256
Naringin,3TMS,isomer #50C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4548.5Semi standard non polar33892256
Naringin,3TMS,isomer #51C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4543.0Semi standard non polar33892256
Naringin,3TMS,isomer #52C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4550.1Semi standard non polar33892256
Naringin,3TMS,isomer #53C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4593.3Semi standard non polar33892256
Naringin,3TMS,isomer #54C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4586.3Semi standard non polar33892256
Naringin,3TMS,isomer #55C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4590.6Semi standard non polar33892256
Naringin,3TMS,isomer #56C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4561.2Semi standard non polar33892256
Naringin,3TMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4538.2Semi standard non polar33892256
Naringin,3TMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4584.8Semi standard non polar33892256
Naringin,3TMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4589.6Semi standard non polar33892256
Naringin,3TMS,isomer #9C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4570.3Semi standard non polar33892256
Naringin,4TMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4507.5Semi standard non polar33892256
Naringin,4TMS,isomer #10C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4442.5Semi standard non polar33892256
Naringin,4TMS,isomer #11C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4422.1Semi standard non polar33892256
Naringin,4TMS,isomer #12C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4449.8Semi standard non polar33892256
Naringin,4TMS,isomer #13C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4430.5Semi standard non polar33892256
Naringin,4TMS,isomer #14C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4411.7Semi standard non polar33892256
Naringin,4TMS,isomer #15C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4427.7Semi standard non polar33892256
Naringin,4TMS,isomer #16C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4546.5Semi standard non polar33892256
Naringin,4TMS,isomer #17C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4499.6Semi standard non polar33892256
Naringin,4TMS,isomer #18C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4492.7Semi standard non polar33892256
Naringin,4TMS,isomer #19C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4515.1Semi standard non polar33892256
Naringin,4TMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4507.5Semi standard non polar33892256
Naringin,4TMS,isomer #20C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4495.3Semi standard non polar33892256
Naringin,4TMS,isomer #21C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4486.4Semi standard non polar33892256
Naringin,4TMS,isomer #22C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4505.3Semi standard non polar33892256
Naringin,4TMS,isomer #23C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4496.2Semi standard non polar33892256
Naringin,4TMS,isomer #24C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4483.1Semi standard non polar33892256
Naringin,4TMS,isomer #25C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4498.0Semi standard non polar33892256
Naringin,4TMS,isomer #26C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4490.7Semi standard non polar33892256
Naringin,4TMS,isomer #27C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4469.6Semi standard non polar33892256
Naringin,4TMS,isomer #28C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4503.1Semi standard non polar33892256
Naringin,4TMS,isomer #29C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4449.0Semi standard non polar33892256
Naringin,4TMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4495.2Semi standard non polar33892256
Naringin,4TMS,isomer #30C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4433.3Semi standard non polar33892256
Naringin,4TMS,isomer #31C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4453.0Semi standard non polar33892256
Naringin,4TMS,isomer #32C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4442.8Semi standard non polar33892256
Naringin,4TMS,isomer #33C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4427.7Semi standard non polar33892256
Naringin,4TMS,isomer #34C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4446.1Semi standard non polar33892256
Naringin,4TMS,isomer #35C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4436.0Semi standard non polar33892256
Naringin,4TMS,isomer #36C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4526.2Semi standard non polar33892256
Naringin,4TMS,isomer #37C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4499.9Semi standard non polar33892256
Naringin,4TMS,isomer #38C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4500.1Semi standard non polar33892256
Naringin,4TMS,isomer #39C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4516.8Semi standard non polar33892256
Naringin,4TMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4495.4Semi standard non polar33892256
Naringin,4TMS,isomer #40C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4468.3Semi standard non polar33892256
Naringin,4TMS,isomer #41C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4448.7Semi standard non polar33892256
Naringin,4TMS,isomer #42C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4480.7Semi standard non polar33892256
Naringin,4TMS,isomer #43C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4432.8Semi standard non polar33892256
Naringin,4TMS,isomer #44C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4419.8Semi standard non polar33892256
Naringin,4TMS,isomer #45C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4434.5Semi standard non polar33892256
Naringin,4TMS,isomer #46C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4526.6Semi standard non polar33892256
Naringin,4TMS,isomer #47C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4517.3Semi standard non polar33892256
Naringin,4TMS,isomer #48C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4541.2Semi standard non polar33892256
Naringin,4TMS,isomer #49C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4498.1Semi standard non polar33892256
Naringin,4TMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4512.4Semi standard non polar33892256
Naringin,4TMS,isomer #50C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4493.6Semi standard non polar33892256
Naringin,4TMS,isomer #51C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4499.6Semi standard non polar33892256
Naringin,4TMS,isomer #52C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4473.3Semi standard non polar33892256
Naringin,4TMS,isomer #53C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4461.8Semi standard non polar33892256
Naringin,4TMS,isomer #54C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4477.0Semi standard non polar33892256
Naringin,4TMS,isomer #55C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4447.0Semi standard non polar33892256
Naringin,4TMS,isomer #56C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4510.9Semi standard non polar33892256
Naringin,4TMS,isomer #57C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4504.8Semi standard non polar33892256
Naringin,4TMS,isomer #58C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4525.3Semi standard non polar33892256
Naringin,4TMS,isomer #59C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4477.0Semi standard non polar33892256
Naringin,4TMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O4500.3Semi standard non polar33892256
Naringin,4TMS,isomer #60C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4458.3Semi standard non polar33892256
Naringin,4TMS,isomer #61C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4475.8Semi standard non polar33892256
Naringin,4TMS,isomer #62C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4517.8Semi standard non polar33892256
Naringin,4TMS,isomer #63C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4509.9Semi standard non polar33892256
Naringin,4TMS,isomer #64C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4520.5Semi standard non polar33892256
Naringin,4TMS,isomer #65C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4491.7Semi standard non polar33892256
Naringin,4TMS,isomer #66C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O4514.5Semi standard non polar33892256
Naringin,4TMS,isomer #67C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C4506.9Semi standard non polar33892256
Naringin,4TMS,isomer #68C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4515.7Semi standard non polar33892256
Naringin,4TMS,isomer #69C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4464.7Semi standard non polar33892256
Naringin,4TMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O4451.6Semi standard non polar33892256
Naringin,4TMS,isomer #70C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C4509.4Semi standard non polar33892256
Naringin,4TMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O4431.7Semi standard non polar33892256
Naringin,4TMS,isomer #9C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C)=C3)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C4460.9Semi standard non polar33892256
Naringin,1TBDMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O4976.5Semi standard non polar33892256
Naringin,1TBDMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O4985.1Semi standard non polar33892256
Naringin,1TBDMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5007.7Semi standard non polar33892256
Naringin,1TBDMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5008.0Semi standard non polar33892256
Naringin,1TBDMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5069.1Semi standard non polar33892256
Naringin,1TBDMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O4988.3Semi standard non polar33892256
Naringin,1TBDMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O4991.2Semi standard non polar33892256
Naringin,1TBDMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5009.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #1C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O5072.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #10C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5088.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #11C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O5062.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #12C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5056.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #13C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5077.5Semi standard non polar33892256
Naringin,2TBDMS,isomer #14C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5092.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #15C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5149.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #16C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O5084.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #17C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5081.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #18C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5103.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #19C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5159.1Semi standard non polar33892256
Naringin,2TBDMS,isomer #2C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O5131.4Semi standard non polar33892256
Naringin,2TBDMS,isomer #20C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O5083.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #21C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5087.1Semi standard non polar33892256
Naringin,2TBDMS,isomer #22C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5107.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #23C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O5149.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #24C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5148.8Semi standard non polar33892256
Naringin,2TBDMS,isomer #25C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5168.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #26C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5076.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #27C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5084.4Semi standard non polar33892256
Naringin,2TBDMS,isomer #28C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C5088.9Semi standard non polar33892256
Naringin,2TBDMS,isomer #3C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O5074.3Semi standard non polar33892256
Naringin,2TBDMS,isomer #4C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O5061.0Semi standard non polar33892256
Naringin,2TBDMS,isomer #5C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O5067.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #6C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O5053.7Semi standard non polar33892256
Naringin,2TBDMS,isomer #7C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O)C=C5)OC4=C3)O[C@H](CO)[C@@H](O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C5073.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #8C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C(=O)C[C@@H](C5=CC=C(O)C=C5)O4)C(O[Si](C)(C)C(C)(C)C)=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5071.2Semi standard non polar33892256
Naringin,2TBDMS,isomer #9C[C@@H]1O[C@@H](O[C@H]2[C@H](OC3=CC(O)=C4C(=O)C[C@@H](C5=CC=C(O[Si](C)(C)C(C)(C)C)C=C5)OC4=C3)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O5137.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringin GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (Non-derivatized) - 70eV, Positivesplash10-044j-9521280000-3e3e40b7d28b4e9032162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (1 TMS) - 70eV, Positivesplash10-00ei-9302015000-e97b650a0d6a1b78ddc32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS ("Naringin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringin GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0000090000-62ab85e8b85e9515ddc12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negative-QTOFsplash10-004i-0000091000-2671e4ecb91933035e782012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0100090000-0c16a31fd116a04809ff2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0100090000-0c16a31fd116a04809ff2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 40V, Negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 10V, Negative-QTOFsplash10-004i-0000090000-4498c4e102c3c7d3d5142017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 20V, Negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 30V, Negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin ESI-TOF 50V, Negative-QTOFsplash10-0fk9-0690000000-3d8f024f57318d3dbca82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-qTof , Positive-QTOFsplash10-0fk9-2981000000-e103705338e8e88553072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-00di-0290110000-a72cef11c1816469a2692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0000090000-4498c4e102c3c7d3d5142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0000090000-d6285c4e4374990ed1612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringin LC-ESI-TOF , negative-QTOFsplash10-004i-0030290000-06238e4a98a4daad32652017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 10V, Positive-QTOFsplash10-00xr-0390740000-ed6375341eb1bebac3192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 20V, Positive-QTOFsplash10-05fr-0490200000-bbf5e62f8ba5ef5c55c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 40V, Positive-QTOFsplash10-01b9-0940000000-043fddfc9269db83e1f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 10V, Negative-QTOFsplash10-02or-3592880000-a3ec8e8504154578e09f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 20V, Negative-QTOFsplash10-0229-2691310000-865585e62bd05144335b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringin 40V, Negative-QTOFsplash10-00di-7590000000-82ba5c0120e07b81e87b2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 208 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID208
FooDB IDFDB011866
KNApSAcK IDC00000983
Chemspider ID390868
KEGG Compound IDC09789
BioCyc IDNARINGIN
BiGG IDNot Available
Wikipedia LinkNaringin
METLIN ID3604
PubChem Compound442428
PDB IDNot Available
ChEBI ID28819
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1400021
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]
  2. Ishii K, Furuta T, Kasuya Y: Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Aug 30;683(2):225-9. [PubMed:8891919 ]
  3. Fuhr U, Kummert AL: The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther. 1995 Oct;58(4):365-73. [PubMed:7586927 ]
  4. Tanaka S, Sato T, Akimoto N, Yano M, Ito A: Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Biochem Pharmacol. 2004 Aug 1;68(3):433-9. [PubMed:15242810 ]
  5. Zhang J, Brodbelt JS: Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. [PubMed:15565223 ]
  6. Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M: The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Jpn J Cancer Res. 2001 Dec;92(12):1322-8. [PubMed:11749698 ]
  7. Ishii K, Furuta T, Kasuya Y: Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine. J Agric Food Chem. 2000 Jan;48(1):56-9. [PubMed:10637051 ]
  8. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81. [PubMed:15351063 ]