Details of the Drug

General Information of Drug (ID: DM3NC4M)

Drug Name

Quercetin

Synonyms

Kvercetin; Meletin; QUE; Quercetine; Quercetol; Quercitin; Quertin; Quertine; Sophoretin; Xanthaurine; Flavin meletin; Kvercetin [Czech]; Quercetin content; Quercetin dihydrate; CI Natural Yellow 10; Cyanidelonon 1522; KUC104418N; KUC107684N; MixCom3_000183; Natural Yellow 10; P0042; Q 0125; TNP00070; TNP00089; LIM-5662; LNS-5662; C.I . natural yellow 10; C.I. 75670; C.I. Natural Yellow 10; C.I. Natural red 1; CU-01000012502-3; KSC-10-126; KSC-23-76; T-Gelb bzw. grun 1; C.I. Natural yellow 10 & 13; 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one dihydrate; 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one; 3',4',5,7-Tetrahydroxyflavan-3-ol; 3',4',5,7-tetrahydroxyflavon-3-ol; 3,3',4',5,7-Pentahydroxyflavone dihydrate; 3,5,7,3',4'-Pentahydroxyflavone; 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on; 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one

Indication

Disease Entry	ICD 11	Status	REF
Obesity	5B81	Approved	[1]
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Therapeutic Class

Hypoglycemic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

302.23

Logarithm of the Partition Coefficient (xlogp)

1.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The drug present in the plasma can be removed from the body at the rate of 11 mL/min/kg [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 0.6 hours [2]
Unbound Fraction: The unbound fraction of drug in plasma is 0.009% [2]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.12 L/kg [2]

Chemical Identifiers

Formula: C15H10O7
IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
InChI: InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
InChIKey: REFJWTPEDVJJIY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5280343
ChEBI ID: CHEBI:16243
CAS Number: 117-39-5
DrugBank ID: DB04216
TTD ID: D0K8KX
VARIDT ID: DR00225
INTEDE ID: DR2630

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Acetyl-CoA:lyso-PAF acetyltransferase (PCAT)	TTPOI4B	PCAT1_HUMAN ; PCAT2_HUMAN	Inhibitor	[3]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Feline leukemia virus subgroup C receptor-related protein 1 (SLC49A1)	DTH6X7Q	FLVC1_HUMAN	Substrate	[4]
Monocarboxylate transporter 2 (SLC16A7)	DTLT3UG	MOT2_HUMAN	Substrate	[5]
Glucose transporter type 1, erythrocyte/brain (SLC2A1)	DTG3T6X	GTR1_HUMAN	Substrate	[6]
Multidrug resistance-associated protein 4 (ABCC4)	DTCSGPB	MRP4_HUMAN	Substrate	[7]
Multidrug resistance-associated protein 1 (ABCC1)	DTSYQGK	MRP1_HUMAN	Substrate	[7]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[8]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[9]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
(Lyso)-N-acylphosphatidylethanolamine lipase (ABHD4)	OTQK3M9X	ABHD4_HUMAN	Gene/Protein Processing	[10]
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1)	OTG2T749	CP24A_HUMAN	Gene/Protein Processing	[10]
1,4-alpha-glucan-branching enzyme (GBE1)	OTK2N05B	GLGB_HUMAN	Gene/Protein Processing	[11]
1-acylglycerol-3-phosphate O-acyltransferase ABHD5 (ABHD5)	OTY829Z3	ABHD5_HUMAN	Gene/Protein Processing	[10]
1-acylglycerol-3-phosphate O-acyltransferase PNPLA3 (PNPLA3)	OTR4990X	PLPL3_HUMAN	Gene/Protein Processing	[10]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1)	OT9HYT7A	PLCB1_HUMAN	Gene/Protein Processing	[10]
10 kDa heat shock protein, mitochondrial (HSPE1)	OT7JSZLB	CH10_HUMAN	Gene/Protein Processing	[12]
14-3-3 protein sigma (SFN)	OTLJCZ1U	1433S_HUMAN	Gene/Protein Processing	[13]
14-3-3 protein theta	OTWG7F3H	1433T_HUMAN	Gene/Protein Processing	[14]
14-3-3 protein zeta/delta	OT2TKG9P	1433Z_HUMAN	Gene/Protein Processing	[15]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5346).
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	Modulation by flavonoids of PAF and related phospholipids in endothelial cells during oxidative stress. J Lipid Res. 2003 Feb;44(2):380-7.
4	The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 2.A.1.28.1)
5	Monocarboxylate Transporters in Drug Disposition: Role in the Toxicokinetics and Toxicodynamics of the Drug of Abuse GHB.
6	Oral Bioavailability and Disposition of Phytochemicals
7	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
8	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
9	Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604.
10	Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
11	Hypoxia-inducible factor-1 (HIF-1) pathway activation by quercetin in human lens epithelial cells. Exp Eye Res. 2009 Dec;89(6):995-1002. doi: 10.1016/j.exer.2009.08.011. Epub 2009 Sep 1.
12	Differential protein expression of peroxiredoxin I and II by benzo(a)pyrene and quercetin treatment in 22Rv1 and PrEC prostate cell lines. Toxicol Appl Pharmacol. 2007 Apr 15;220(2):197-210. doi: 10.1016/j.taap.2006.12.030. Epub 2007 Jan 9.
13	Flavones and flavonols exert cytotoxic effects on a human oesophageal adenocarcinoma cell line (OE33) by causing G2/M arrest and inducing apoptosis. Food Chem Toxicol. 2008 Jun;46(6):2042-53. doi: 10.1016/j.fct.2008.01.049. Epub 2008 Feb 7.
14	Quercetin potentiates apoptosis by inhibiting nuclear factor-kappaB signaling in H460 lung cancer cells. Biol Pharm Bull. 2013;36(6):944-51. doi: 10.1248/bpb.b12-01004.
15	Quercetin acts via the G3BP1/YWHAZ axis to inhibit glycolysis and proliferation in oral squamous cell carcinoma. Toxicol Mech Methods. 2023 Feb;33(2):141-150. doi: 10.1080/15376516.2022.2103480. Epub 2022 Aug 9.