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]
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Therapeutic Class

Anticholesteremic Agents

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: CHEBI:28230
CAS Number: 520-33-2
DrugBank ID: DB01094
TTD ID: D07MGA
VARIDT ID: DR00557
INTEDE ID: DR0808

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]

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Drug Transporter (DTP)

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

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Adiponectin (ADIPOQ)	OTNX23LE	ADIPO_HUMAN	Gene/Protein Processing	[5]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[5]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[6]
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[7]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[6]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Gene/Protein Processing	[6]
CCAAT/enhancer-binding protein alpha (CEBPA)	OTOM9OE4	CEBPA_HUMAN	Gene/Protein Processing	[5]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[8]
Copper chaperone for superoxide dismutase (CCS)	OTXHT3QO	CCS_HUMAN	Protein Interaction/Cellular Processes	[8]
Cyclin-dependent kinase 2 (CDK2)	OTB5DYYZ	CDK2_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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	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.
7	Inhibition of aromatase activity by flavonoids. Arch Pharm Res. 1999 Jun;22(3):309-12.
8	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.
9	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.