precursor

Showing entry for Hesperidin

Identification

PhytoHub ID
PHUB000381
Name
Hesperidin
Systematic Name
Not Available
Synonyms
  • Ciratin
  • Hesperetin 7-O-rutinoside
CAS Number
Not Available
Average Mass
610.565
Monoisotopic Mass
610.189770395
Chemical Formula
C28H34O15
IUPAC Name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
InChI Key
QUQPHWDTPGMPEX-LLHRBZKSSA-N
InChI Identifier
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17?,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
SMILES
COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
2.69e+00 g/l
LogS (ALOGPS)
-2.36
LogP (ALOGPS)
-0.27
Hydrogen Acceptors
15
Hydrogen Donors
8
Rotatable Bond Count
7
Polar Surface Area
234.28999999999996
Refractivity
140.76700000000005
Polarizability
60.286453888810016
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.612182351683661
pKa (strongest acidic)
8.609445995469542
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", "3'-hydroxyflavonoids", "4'-O-methylated flavonoids", "5-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Anisoles", "Aryl alkyl ketones", "Chromones", "Disaccharides", "Flavanones", "Hydrocarbon derivatives", "Methoxybenzenes", "Methoxyphenols", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Phenolic glycosides", "Phenoxy compounds", "Polyols", "Secondary alcohols", "Vinylogous acids"]
External Descriptor Annotations
Not Available
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3'-hydroxyflavonoid", "4p-methoxyflavonoid-skeleton", "5-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Anisole", "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", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenolic glycoside", "Phenoxy compound", "Polyol", "Secondary alcohol", "Vinylogous acid"]

Spectra from Online Resources

Record IDSourceDescriptionView
BML00642MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00653MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00664MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML00674MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00682MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00690MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML81385MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML81386MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
FIO00483MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00484MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00485MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00486MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00487MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00488MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00489MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00490MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00491MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00492MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
PM000507ReSpectN/A Spectrum - 35%, [M+H]+View Spectra
PR100354MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100801MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PS084907ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS084908ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS084909ReSpectN/A Spectrum - 30, [M-H]-View Spectra
PS084910ReSpectN/A Spectrum - 40, [M-H]-View Spectra
PS084911ReSpectN/A Spectrum - 50, [M-H]-View Spectra
PS084912ReSpectN/A Spectrum - 60, [M-H]-View Spectra
TY000026MassBankLC-ESI-ITTOF Spectrum - -, [M-H]-View Spectra
TY000027MassBankLC-ESI-ITTOF Spectrum - -, [M-H]-View Spectra
TY000035MassBankLC-ESI-ITTOF Spectrum - -, [M+H]+View Spectra
TY000036MassBankLC-ESI-ITTOF Spectrum - -, [M+H]+View Spectra
TY000205MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra
TY000206MassBankLC-ESI-ITTOF Spectrum - -, unspecifiedView Spectra

Food Sources

NameGroup
Grapefruit juiceBeverages, Non-alcoholic PublicationsShow
Orange juiceBeverages, Non-alcoholic PublicationsShow
Sweet orangeFruit, CitrusShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Hesperidin Hesperetinhumanplasma, urinegut microbiota metabolite5h-8h200-500 nmol/L5-10%C16H14O6302.079038171 Detailed Intervention Studies Publications
Hesperidin 3-(3'-Hydroxy-4'-methoxyphenyl)hydracrylic acidhumanurine (major)gut microbiota metaboliteNot AvailableNot AvailableNot AvailableC10H12O5212.068473486 Publications
Hesperidin Hesperetin-3',7-diglucuronideratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC28H30O18654.143214126 Publications
Hesperidin Hesperetin-3'-glucuronidehuman ratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Detailed Intervention Studies Publications
Hesperidin Hesperetin-3'-sulfatehumanplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC16H14O9S382.035853205 Detailed Intervention Studies Publications
Hesperidin Hesperetin 5,7-diglucuronidehuman ratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC28H30O18654.143214126 Publications
Hesperidin Hesperetin-7-glucuronidehuman ratplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC22H22O12478.111126148 Detailed Intervention Studies Publications
Hesperidin Hesperetin glucuronidehumanurinehost metabolismNot AvailableNot Available1-5%C22H22O12478.4099437 Publications
Hesperidin Hesperetin sulfoglucuronidehuman ratplasma, urinehost metabolismNot AvailableNot Available<1%C22H22O15S558.4722484 Detailed Intervention Studies Publications
Hesperidin Hesperetin-5-sulfatehumanplasma, urinehost metabolismNot AvailableNot AvailableNot AvailableC16H14O9S382.035853205 Publications
Hesperidin Dihydroisoferulic acidin vitro (human)Not AvailableNot AvailableNot AvailableNot AvailableNot AvailableC10H12O4196.073558866 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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