Details of the Drug

General Information of Drug (ID: DMR8YD6)

Drug Name

B-Lactams

Synonyms

Luteolin; luteolin; 491-70-3; Luteolol; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; Luteoline; Digitoflavone; Flacitran; Weld Lake; Cyanidenon 1470; Salifazide; Yama kariyasu; 5,7,3',4'-Tetrahydroxyflavone; UNII-KUX1ZNC9J2; CI Natural Yellow 2; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; 7-Tetrahydroxyflavone; CCRIS 3790; EINECS 207-741-0; KUX1ZNC9J2; CHEMBL151; BRN 0292084; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

286.24

Topological Polar Surface Area (xlogp)

1.4

Rotatable Bond Count (rotbonds)

1

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C15H10O6
IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChI: InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
InChIKey: IQPNAANSBPBGFQ-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5280445
ChEBI ID: CHEBI:15864
CAS Number: 491-70-3
TTD ID: D04AIT

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	[2]
Bacterial DD-carboxypeptidase (Bact vanYB)	TTLP6GN	VANY_ENTFA	Inhibitor	[1]
DNA topoisomerase I (TOP1)	TTGTQHC	TOP1_HUMAN	Inhibitor	[3]

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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

Bacterial infection

ICD Disease Classification

1A00-1C4Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
DNA topoisomerase I (TOP1)	DTT	TOP1	6.65E-01	0.2	0.39

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
2	Inhibition of lysoPAF acetyltransferase activity by flavonoids. Inflamm Res. 1996 Nov;45(11):546-9.
3	Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. Biochem J. 2002 Sep 1;366(Pt 2):653-61.
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	Impact of natural products on developing new anti-cancer agents. Chem Rev. 2009 Jul;109(7):3012-43.
6	Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
7	Characterization of protein kinase chk1 essential for the cell cycle checkpoint after exposure of human head and neck carcinoma A253 cells to a novel topoisomerase I inhibitor BNP1350. Mol Pharmacol.2000 Mar;57(3):453-9.
8	Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer. 2006 Oct;6(10):789-802.
9	Phase I study of topoisomerase I inhibitor exatecan mesylate (DX-8951f) given as weekly 24-hour infusions three of every four weeks. Clin Cancer Res. 2001 Dec;7(12):3963-70.
10	Edotecarin: a novel topoisomerase I inhibitor. Clin Colorectal Cancer. 2005 May;5(1):27-36.
11	Rubitecan. Expert Opin Investig Drugs. 2006 Jan;15(1):71-9.
12	Nonclinical pharmacokinetics and activity of etirinotecan pegol (NKTR-102), a long-acting topoisomerase 1 inhibitor, in multiple cancer models. Cancer Chemother Pharmacol. 2014 Dec;74(6):1125-37.
13	Modulation by flavonoids of PAF and related phospholipids in endothelial cells during oxidative stress. J Lipid Res. 2003 Feb;44(2):380-7.
14	Binding of cephalothin and cefotaxime to D-ala-D-ala-peptidase reveals a functional basis of a natural mutation in a low-affinity penicillin-binding protein and in extended-spectrum beta-lactamases. Biochemistry. 1995 Jul 25;34(29):9532-40.
15	A 1.2-A snapshot of the final step of bacterial cell wall biosynthesis. Proc Natl Acad Sci U S A. 2001 Feb 13;98(4):1427-31.
16	Extended-spectrum cephalosporinases: structure, detection and epidemiology. Future Microbiol. 2007 Jun;2:297-307.
17	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
18	Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors. J Med Chem. 2009 Oct 8;52(19):6097-106.
19	DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
20	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
21	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.