Details of the Drug

General Information of Drug (ID: DMKER83)

Drug Name
Hesperetin
Synonyms
Hesperin; Hesperitin; TNP00238; YSO2; Cyanidanon 4'-methyl ether 1626; Flavanone, 3',5,7-trihydroxy-4'-methoxy-(VAN); Flavanone, 3',5,7-trihydroxy-4'-methoxy-(VAN) (8CI); (-)-hesperetin; (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one; (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one; (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone; (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; 3',5,7-Trihydroxy-4'-methoxyflavanone; 3',5,7-Trihydroxy-4-methoxyflavanone; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-(9CI); 5,7,3'-Trihydroxy-4'-methoxyflavanone
Indication
Disease Entry ICD 11 Status REF
High blood cholesterol level 5C80.00 Approved [1]
Therapeutic Class
Anticholesteremic Agents
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 302.28
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C16H14O6
IUPAC Name
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Canonical SMILES
COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N
Cross-matching ID
PubChem CID
72281
ChEBI ID
CHEMBL399121
CAS Number
520-33-2
UNII
Q9Q3D557F1
DrugBank ID
DB01094
TTD ID
D07MGA
VARIDT ID
DR00557
INTEDE ID
DR0808
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Diacylglycerol acyltransferase 1 (DGAT1) TTF8P9I DGAT1_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2)
Main DME 		DEJGDUW CP1A2_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
CCAAT/enhancer-binding protein alpha (CEBPA) OTOM9OE4 CEBPA_HUMAN Gene/Protein Processing [5]
Copper chaperone for superoxide dismutase (CCS) OTXHT3QO CCS_HUMAN Protein Interaction/Cellular Processes [6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [7]
Cytochrome b-c1 complex subunit Rieske, mitochondrial OTA2AXFN UCRI_HUMAN Protein Interaction/Cellular Processes [6]
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Gene/Protein Processing [8]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [9]
Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial (ALDH4A1) OT25Z6XH AL4A1_HUMAN Protein Interaction/Cellular Processes [6]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [6]
DNA repair nuclease/redox regulator APEX1 (APEX1) OT53OI14 APEX1_HUMAN Protein Interaction/Cellular Processes [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease High blood cholesterol level
ICD Disease Classification 5C80.00
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Diacylglycerol acyltransferase 1 (DGAT1) DTT DGAT1 3.51E-01 -0.41 -0.62
Breast cancer resistance protein (ABCG2) DTP BCRP 1.85E-01 -1.34E-01 -4.20E-01
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 5.25E-01 -4.04E-01 -5.29E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drug information of Hesperetin, 2008. eduDrugs.
2 In vitro inhibition of diacylglycerol acyltransferase by prenylflavonoids from Sophora flavescens. Planta Med. 2004 Mar;70(3):258-60.
3 Interaction of the breast cancer resistance protein with plant polyphenols. Biochem Biophys Res Commun. 2004 Apr 23;317(1):269-75.
4 In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem Toxicol. 2002 May;40(5):609-16.
5 Hesperetin inhibit adipocyte differentiation and enhance Bax- and p21-mediated adipolysis in human mesenchymal stem cell adipogenesis. J Biochem Mol Toxicol. 2015 Mar;29(3):99-108. doi: 10.1002/jbt.21672. Epub 2014 Oct 26.
6 Various concentrations of hesperetin induce different types of programmed cell death in human breast cancerous and normal cell lines in a ROS-dependent manner. Chem Biol Interact. 2023 Sep 1;382:110642. doi: 10.1016/j.cbi.2023.110642. Epub 2023 Jul 23.
7 Hesperetin induced G1-phase cell cycle arrest in human breast cancer MCF-7 cells: involvement of CDK4 and p21. Nutr Cancer. 2007;59(1):115-9. doi: 10.1080/01635580701419030.
8 Role of hesperetin (a natural flavonoid) and its analogue on apoptosis in HT-29 human colon adenocarcinoma cell line--a comparative study. Food Chem Toxicol. 2012 Mar;50(3-4):660-71.
9 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.