Hesperidin

Identification

Name
Hesperidin
Accession Number
DB04703
Type
Small Molecule
Groups
Approved, Investigational
Description

Hesperidin is a flavan-on glycoside found in citrus fruits.

Structure
Thumb
Synonyms
  • (S)-(−)-hesperidin
  • Cirantin
  • Ciratin
  • Hesperetin 7-O-rutinoside
  • Hesperidin
  • Hesperidoside
External IDs
NDI 590 / NSC-44184
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Cilobana Cpa TabHesperidin (75 mg) + Ascorbic acid (150 mg) + Bromelains (4 mg) + Citrus bioflavonoids (75 mg) + Vitamin A (10000 unit)TabletOralAnabolic Laboratories Inc.1968-12-311996-10-02Canada
Rose Hips 500plus Nu LifeHesperidin (100 mg) + Ascorbic acid (500 mg) + Citrus bioflavonoids (100 mg) + Rutin (50 mg)TabletOralNu Life Nutrition Ltd.1972-12-312005-03-15Canada
Special CHesperidin (32.5 mg) + Ascorbic acid (333 mg) + Citrus bioflavonoids (12.5 mg)CapsuleOralAnabolic Laboratories Inc.1963-12-311996-10-02Canada
Categories
UNII
E750O06Y6O
CAS number
520-26-3
Weight
Average: 610.5606
Monoisotopic: 610.189770418
Chemical Formula
C28H34O15
InChI Key
QUQPHWDTPGMPEX-QJBIFVCTSA-N
InChI
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
IUPAC Name
(2S)-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
SMILES
COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C=C2O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAurora kinase BNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hiromi Hijiya, Toshio Miyake, ".alpha.-glycosyl hesperidin, and its preparation and uses." U.S. Patent US5652124, issued June, 1983.

US5652124
General References
Not Available
External Links
KEGG Drug
D01038
KEGG Compound
C09755
PubChem Compound
10621
PubChem Substance
46506898
ChemSpider
10176
BindingDB
61776
ChEBI
28775
ChEMBL
CHEMBL449317
PharmGKB
PA449867
HET
H1N
Wikipedia
Hesperidin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentEndothelial Dysfunction / Metabolic Syndromes1
2WithdrawnTreatmentBMI >30 kg/m2 / Insulin Resistance1
3CompletedPreventionOsteoporosis, Osteopenia1
3Unknown StatusTreatmentChronic Venous Insufficiency (CVI) / Diseases1
4CompletedTreatmentIncompetent accessory saphenous veins1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.69 mg/mLALOGPS
logP-0.27ALOGPS
logP-0.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity140.77 m3·mol-1ChemAxon
Polarizability58.76 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0000009000-8c42f8adffac7d78b94c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0zfr-0006009000-1f68460ef007fbd1cfa9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009002000-26d653ee690ce5c6cd20
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0009000000-a4d68b31e046fbf057d6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0019000000-e9135e61d5aa11f40135
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0119003000-80c5f918f82d46fc1131
LC-MS/MS Spectrum - LC-ESI-ITTOF , negativeLC-MS/MSsplash10-0udi-0029000000-15e7bff1df4ba788d095
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ika-0003906000-8e92397c3ef59083d90b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0109500000-d16e1ccb83edc18c2285
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0109000000-44829065079eda0599e1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0209000000-edd02887a04b421dbb39
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0819000000-3ad8fb39515b5eaa0fd2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-3719300000-f2635b73560ddfd8533f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-2924000000-2288595ee1b67877de4b
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavonoid glycosides
Direct Parent
Flavonoid-7-O-glycosides
Alternative Parents
4'-O-methylated flavonoids / 3'-hydroxyflavonoids / 5-hydroxyflavonoids / Flavanones / Phenolic glycosides / O-glycosyl compounds / Disaccharides / Chromones / Methoxyphenols / Phenoxy compounds
show 14 more
Substituents
Flavonoid-7-o-glycoside / 4p-methoxyflavonoid-skeleton / 3'-hydroxyflavonoid / 5-hydroxyflavonoid / Flavanone / Hydroxyflavonoid / Flavan / Phenolic glycoside / Chromone / Disaccharide
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rutinoside, disaccharide derivative, 3'-hydroxyflavanones, monomethoxyflavanone, flavanone glycoside, dihydroxyflavanone (CHEBI:28775) / flavanones (C09755)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine/tyrosine kinase activity
Specific Function
Serine/threonine-protein kinase component of the chromosomal passenger complex (CPC), a complex that acts as a key regulator of mitosis. The CPC complex has essential functions at the centromere in...
Gene Name
AURKB
Uniprot ID
Q96GD4
Uniprot Name
Aurora kinase B
Molecular Weight
39310.195 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 11, 2007 11:49 / Updated on October 01, 2018 13:54