Hesperidin

Identification

Summary

Hesperidin is a bioflavonoid found in a variety of nutritional supplements that is touted to have various beneficial effects on blood vessel disorders and various other conditions.

Generic Name
Hesperidin
DrugBank Accession Number
DB04703
Background

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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 610.5606
Monoisotopic: 610.189770418
Chemical Formula
C28H34O15
Synonyms
  • (S)-(−)-hesperidin
  • Cirantin
  • Ciratin
  • Hesperetin 7-O-rutinoside
  • Hesperidin
  • Hesperidina
  • Hesperidoside
External IDs
  • NDI 590
  • NSC-44184

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageCapillary fragilityCombination Product in combination with: Diosmin (DB08995)••••••••••••••••••
Used in combination to manageVenous insufficiencyCombination Product in combination with: Diosmin (DB08995)••••••••••••••••••
Symptomatic treatment ofVaricosities•••••••••••••••••••• ••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAurora kinase B
regulator
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AVEFLON TABLETHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralAPEX PHARMACY MARKETING SDN. BHD.2020-09-08Not applicableMalaysia flag
Cilobana Cpa TabHesperidin (75 mg / tab) + Ascorbic acid (150 mg / tab) + Bromelains (4 mg / tab) + Citrus bioflavonoids (75 mg / tab) + Vitamin A (10000 unit / tab)TabletOralAnabolic Laboratories Inc.1968-12-311996-10-02Canada flag
Daflon 1000mg Film-Coated TabletHesperidin (100 mg) + Diosmin (900 mg)Tablet, film coatedOralSERVIER MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag
Daflon 500 mg - FilmtablettenHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralServier Austria Gmb H1994-11-18Not applicableAustria flag
daflon 500mg tabletsHesperidin (50 mg) + Diosmin (450 mg)Tablet, film coatedOralSERVIER MALAYSIA SDN BHD2020-09-08Not applicableMalaysia flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
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
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
rutinoside, disaccharide derivative, 3'-hydroxyflavanones, monomethoxyflavanone, flavanone glycoside, dihydroxyflavanone (CHEBI:28775) / flavanones (C09755)
Affected organisms
Not Available

Chemical Identifiers

UNII
E750O06Y6O
CAS number
520-26-3
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

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
KEGG Drug
D01038
KEGG Compound
C09755
PubChem Compound
10621
PubChem Substance
46506898
ChemSpider
10176
BindingDB
61776
RxNav
5281
ChEBI
28775
ChEMBL
CHEMBL449317
ZINC
ZINC000008143568
PharmGKB
PA449867
PDBe Ligand
H1N
Wikipedia
Hesperidin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentLymphedema Lower Extremity1
4CompletedTreatmentVenous Insufficiency1
4Not Yet RecruitingTreatmentAnal Fistulas1
4Unknown StatusTreatmentPelvic Congestive Syndrome / Pelvic Varicose Veins / Venous Disease1
3CompletedPreventionOsteoporosis, Osteopenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
SuspensionOral1000 mg
Tablet, sugar coatedOral
Tablet, coatedOral
Tablet, delayed releaseOral
TabletOral900.000 mg
SuspensionOral
Tablet, coatedOral500 mg
TabletOral
Tablet, film coated
Tablet, extended releaseOral
Capsule, liquid filledOral500 mg
Tablet, film coatedOral450 mg
CapsuleOral
TabletOral450.000 mg
Powder, for suspensionOral
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)8.61Chemaxon
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
Polarizability58.87 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
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-0a4i-0960000000-19057cfec7c79b016a55
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSsplash10-0udi-0009000000-283330c229581467aa8c
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0002009000-ef46dd12935025cc99f3
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0udi-0009002000-4750b2aa846256abc7dc
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0a4i-0010009000-7d463589853787a4d83a
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSsplash10-0udi-0029000000-5abbbe61f9472ac9f446
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSsplash10-0udi-0009000000-865b6028ed5cc1fd73d8
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0udi-2924000000-2288595ee1b67877de4b
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0j4i-0808869000-fc299cc407bfa68127ff
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0035049000-82f20d1b152c9bfc4edd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0i09-0924632000-1f1b52b29a35b7f3f1f4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0224945000-85b28fda4fd5f8d5ca45
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02dj-1629623000-201f1a33c6254d503449
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pxr-0391000000-eb1a81336a265a60b573
13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-255.8648737
predicted
DarkChem Lite v0.1.0
[M-H]-247.5912737
predicted
DarkChem Lite v0.1.0
[M-H]-222.63536
predicted
DeepCCS 1.0 (2019)
[M+H]+255.2088737
predicted
DarkChem Lite v0.1.0
[M+H]+247.5176737
predicted
DarkChem Lite v0.1.0
[M+H]+224.53075
predicted
DeepCCS 1.0 (2019)
[M+Na]+255.4858737
predicted
DarkChem Lite v0.1.0
[M+Na]+230.43336
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
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. [Article]
  2. de Groot CO, Hsia JE, Anzola JV, Motamedi A, Yoon M, Wong YL, Jenkins D, Lee HJ, Martinez MB, Davis RL, Gahman TC, Desai A, Shiau AK: A Cell Biologist's Field Guide to Aurora Kinase Inhibitors. Front Oncol. 2015 Dec 21;5:285. doi: 10.3389/fonc.2015.00285. eCollection 2015. [Article]

Drug created at September 11, 2007 17:49 / Updated at April 30, 2021 13:05