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Natural Product (NP) Details

General Information of the NP (ID: NP5470)
Name
Hesperidin
Synonyms
Cirantin; Hesperidoside; Hesper bitabs; Hesperetin-rutinosid; Hesperidine; UNII-E750O06Y6O; CCRIS 3940; (S)-(-)-Hesperidin; EINECS 208-288-1; NSC 44184; BRN 0075140; Hesperidin, (2S)-; Hesperetin 7-rutinoside; MLS001304066; (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]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one; CHEBI:28775; USAF CF-3; Hesperidin, (S)-(-)-; Hesperitin-7-rhamnoglucoside; E750O06Y6O; C28H34O15; HESPERIDINE
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Species Origin Citrus sinensis ...     Click to Show/Hide
Citrus sinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus sinensis
Citrus sinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus sinensis
Citrus trifoliata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus trifoliata
Salvia rosmarinus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Salvia
Species: Salvia rosmarinus
Citrus aurantium
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus aurantium
Citrus reticulata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus reticulata
Citrus reticulata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus reticulata
Citrus medica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus medica
Clinopodium chinense
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Clinopodium
Species: Clinopodium chinense
Disease Non-thrombocytopenic purpura [ICD-11: 3B60] Approved [1]
Discovery agent [ICD-11: N.A.] Investigative [2]
Structure
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2D MOL

3D MOL

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Formula
C28H34O15
PubChem CID
10621
Canonical SMILES
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
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
InChIKey
QUQPHWDTPGMPEX-QJBIFVCTSA-N
CAS Number
CAS 520-26-3
ChEBI ID
CHEBI:28775
Herb ID
HBIN029196
ETMC ID
1370
SymMap ID
SMIT00275
TCMSP ID
MOL007930
TTD Drug ID
D0I9HF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Diethylcarbamazine      Filariasis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression GGT1  Molecule Info 
Pathway MAP
Down-regulation Expression GPT  Molecule Info 
Pathway MAP
Down-regulation Expression GPT  Molecule Info 
Pathway MAP
Down-regulation Expression IL19  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression TGFB1  Molecule Info 
Pathway MAP
                    In-vivo Model Adult male wistar rats (250-275 g) were used in this study.
                    Experimental
                    Result(s)
DEC when combined with HDN blunted EtOH-induced necroinflammation and elevation of liver injury parameters in serum.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vivo Model The 1*106 Ehrlich ascitic tumor cells were transplanted subcutaneously in the left thigh of male albino mice for the experiment.
                    Experimental
                    Result(s)
The use of HES as adjuvant therapy with DOX enhanced the therapeutic efficacy and alleviate the resistance to DOX in treatment of solid tumors.
Target and Pathway
Target(s) Calcium channel alpha-1B (CACNA1B)  Molecule Info  [2]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Calcium signaling pathway
3 Synaptic vesicle cycle
4 Retrograde endocannabinoid signaling
5 Cholinergic synapse
6 Serotonergic synapse
7 GABAergic synapse
8 Dopaminergic synapse
9 Taste transduction
10 Type II diabetes mellitus
11 Morphine addiction
12 Nicotine addiction
Panther Pathway Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway Click to Show/Hide
2 Ionotropic glutamate receptor pathway
3 Metabotropic glutamate receptor group III pathway
4 Metabotropic glutamate receptor group II pathway
5 Thyrotropin-releasing hormone receptor signaling pathway
6 Endogenous cannabinoid signaling
7 GABA-B receptor II signaling
Reactome Depolarization of the Presynaptic Terminal Triggers the Opening of Calcium Channels Click to Show/Hide
WikiPathways Calcium Regulation in the Cardiac Cell Click to Show/Hide
2 Synaptic Vesicle Pathway
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
Reference 3 Antifibrotic effect of diethylcarbamazine combined with hesperidin against ethanol induced liver fibrosis in rats. Biomed Pharmacother. 2017 May;89:1196-1206.
Reference 4 Effect of hesperidin on mice bearing Ehrlich solid carcinoma maintained on doxorubicin. Tumour Biol. 2015 Dec;36(12):9267-75.
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China