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
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 302.28
Topological Polar Surface Area (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]

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]
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.
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16 Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43.
17 The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9.
18 Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10.
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20 Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51.
21 The phytoestrogen genistein enhances multidrug resistance in breast cancer cell lines by translational regulation of ABC transporters. Cancer Lett. 2016 Jun 28;376(1):165-72.
22 Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7.
23 Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2.
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