Identification

PhytoHub ID
PHUB000389
Name
Naringin
Systematic Name
Not Available
Synonyms
  • Naringenin 7-O-neohesperidoside
  • Naringenin 7-O-rhamnoglucoside
CAS Number
Not Available
Average Mass
580.539
Monoisotopic Mass
580.17920571
Chemical Formula
C27H32O14
IUPAC Name
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
InChI Key
DFPMSGMNTNDNHN-JJLSSNRUSA-N
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
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)CC(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
Structure

Calculated Properties

Solubility (ALOGPS)
4.06e+00 g/l
LogS (ALOGPS)
-2.16
LogP (ALOGPS)
-0.24
Hydrogen Acceptors
14
Hydrogen Donors
8
Rotatable Bond Count
6
Polar Surface Area
225.05999999999997
Refractivity
134.30380000000002
Polarizability
56.864154507353646
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-2.981092569339441
pKa (strongest acidic)
8.579343855596704
Number of Rings
5
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanones

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavonoid glycosides
Direct Parent Name
Flavonoid-7-O-glycosides
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Aryl alkyl ketones", "Benzene and substituted derivatives", "Chromones", "Disaccharides", "Flavanones", "Hydrocarbon derivatives", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Polyols", "Primary alcohols", "Secondary alcohols", "Vinylogous acids"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Aromatic heteropolycyclic compound", "Aryl alkyl ketone", "Aryl ketone", "Benzenoid", "Benzopyran", "Chromane", "Chromone", "Disaccharide", "Ether", "Flavan", "Flavanone", "Flavonoid-7-o-glycoside", "Glycosyl compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Ketone", "Monocyclic benzene moiety", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenolic glycoside", "Polyol", "Primary alcohol", "Secondary alcohol", "Vinylogous acid"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML01161MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML01170MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML01179MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81785MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81786MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
CE000186MassBankLC-ESI-ITFT Spectrum - 35eV, unspecifiedView Spectra
CE000187MassBankLC-ESI-ITFT Spectrum - 45eV, unspecifiedView Spectra
CE000188MassBankLC-ESI-ITFT Spectrum - 55eV, unspecifiedView Spectra
CE000189MassBankLC-ESI-ITFT Spectrum - 70eV, unspecifiedView Spectra
CE000190MassBankLC-ESI-ITFT Spectrum - -, unspecifiedView Spectra
PB000783MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB000784MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB000785MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB000801MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB000802MassBankLC-ESI-QTOF Spectrum - 55 eV, unspecifiedView Spectra
PB000803MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB000804MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
PB005722MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
PB005723MassBankLC-ESI-QTOF Spectrum - 15 eV, unspecifiedView Spectra
PB005724MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
PB005725MassBankLC-ESI-QTOF Spectrum - 25 eV, unspecifiedView Spectra
PB005726MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
TY000029MassBankLC-ESI-ITTOF Spectrum - -, [M-H]-View Spectra

Food Sources

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Naringin EriodictyolNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H12O6288.063388106 Detailed Intervention Studies
Naringin Naringeninhumanplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC15H12O5272.068473486 Detailed Intervention Studies Publications
Naringin NaringinhumanurineunchangedNot AvailableNot AvailableNot AvailableC27H32O14580.17920571 Detailed Intervention Studies Publications
Naringin Phloretic acidhumanplasmahost metabolismNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Naringin 3-Phenylpropionic acidhumanplasmagut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O2150.068079562 Publications
Naringin Eriodictyol sulfateNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H12O9S368.3194001 Detailed Intervention Studies
Naringin Naringenin-4'-glucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC21H20O11448.100561464 Detailed Intervention Studies Publications
Naringin Naringenin-7-glucuronidehumanurinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC21H20O11448.100561464 Detailed Intervention Studies Publications
Naringin Naringenin-diglucuronideNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC27H28O17624.5095093 Detailed Intervention Studies
Naringin Naringenin-sulfoglucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC21H20O14S528.4459545 Detailed Intervention Studies Publications
Naringin Naringenin-5-glucuronidehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC21H20O11448.100561464 Detailed Intervention Studies Publications
Naringin Naringenin-7- sulfatehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC15H12O8S352.02528852 Detailed Intervention Studies Publications
Naringin Naringenin-4'-sulfatehumanurinehost metabolismNot AvailableNot AvailableNot AvailableC15H12O8S352.02528852 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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