Details of the Drug

General Information of Drug (ID: DM4C7E6)

Drug Name
BAICALEIN
Synonyms
baicalein; 491-67-8; 5,6,7-Trihydroxyflavone; 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one; Noroxylin; Biacalein; BaiKalein; Baicelein; UNII-49QAH60606; NSC661431; NSC 661431; CHEMBL8260; 5,6,7-trihydroxy-2-phenylchromen-4-one; CHEBI:2979; FXNFHKRTJBSTCS-UHFFFAOYSA-N; MFCD00017459; 4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-phenyl-; 49QAH60606; 5,7-Trihydroxyflavone; 5,6,7-trihydroxy-2-phenyl-chromen-4-one; Sho-saiko-to; SMR000112462; SR-01000597499; Baicalein, 8; Baicalein,(S); 3WL; Baicalein, 14; Baicalein, 98%; AC1NQYPP; Tocris-1761
Indication
Disease Entry ICD 11 Status REF
Influenza virus infection 1E30-1E32 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 270.24
Logarithm of the Partition Coefficient (xlogp) 1.7
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H10O5
IUPAC Name
5,6,7-trihydroxy-2-phenylchromen-4-one
Canonical SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O
InChI
InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
InChIKey
FXNFHKRTJBSTCS-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281605
ChEBI ID
CHEMBL8260
CAS Number
491-67-8
UNII
49QAH60606
DrugBank ID
DB16101
TTD ID
D00YEV
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [2]
L-selectin (SELL) TT2IYXF LYAM1_HUMAN Inhibitor [3]
Lactoylglutathione lyase (GLO1) TTV9A7R LGUL_HUMAN Inhibitor [4]
P-selectin (SELP) TTE5VG0 LYAM3_HUMAN Inhibitor [3]
Prolyl endopeptidase (PREP) TTNGKET PPCE_HUMAN Inhibitor [5]
Tumor necrosis factor (TNF) TTF8CQI TNFA_HUMAN Inhibitor [6]
Xanthine dehydrogenase/oxidase (XDH) TT7RJY8 XDH_HUMAN Inhibitor [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [8]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [11]
Glycogen phosphorylase, brain form (PYGB) OT2ZTJT0 PYGB_HUMAN Gene/Protein Processing [12]
Glycogen phosphorylase, liver form (PYGL) OTS1YFGR PYGL_HUMAN Gene/Protein Processing [12]
Hairy/enhancer-of-split related with YRPW motif protein 1 (HEY1) OTJQL0I3 HEY1_HUMAN Gene/Protein Processing [13]
Hairy/enhancer-of-split related with YRPW motif protein 2 (HEY2) OTU4J3ZI HEY2_HUMAN Gene/Protein Processing [13]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [14]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Influenza virus infection
ICD Disease Classification 1E30-1E32
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prolyl endopeptidase (PREP) DTT PREP 5.70E-01 -0.09 -0.33
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT03830684) A Randomized, Double-blind, Placebo-controlled, Multicenter and Phase IIa Clinical Trial for the Effectiveness and Safety of Baicalein Tablets in the Treatment of Improve Other Aspects of Healthy Adult With Influenza Fever. U.S. National Institutes of Health.
2 Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity. J Med Chem. 1991 Mar;34(3):1028-36.
3 Rational design of novel, potent small molecule pan-selectin antagonists. J Med Chem. 2007 Mar 22;50(6):1101-15.
4 Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects. Bioorg Med Chem. 2008 Apr 1;16(7):3969-75.
5 Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor. Bioorg Med Chem. 2008 Aug 1;16(15):7516-24.
6 Discovery of the inhibitors of tumor necrosis factor alpha with structure-based virtual screening. Bioorg Med Chem Lett. 2010 Nov 1;20(21):6195-8.
7 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
8 Baicalein represses TGF-1-induced fibroblast differentiation through the inhibition of miR-21. Toxicol Appl Pharmacol. 2018 Nov 1;358:35-42. doi: 10.1016/j.taap.2018.09.007. Epub 2018 Sep 7.
9 Structure-activity relationship and mechanism of flavonoids on the inhibitory activity of P-glycoprotein (P-gp)-mediated transport of rhodamine123 and daunorubicin in P-gp overexpressed human mouth epidermal carcinoma (KB/MDR) cells. Food Chem Toxicol. 2021 Sep;155:112381. doi: 10.1016/j.fct.2021.112381. Epub 2021 Jul 1.
10 Baicalein induces cancer cell death and proliferation retardation by the inhibition of CDC2 kinase and survivin associated with opposite role of p38 mitogen-activated protein kinase and AKT. Mol Cancer Ther. 2007 Nov;6(11):3039-48. doi: 10.1158/1535-7163.MCT-07-0281.
11 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.
12 Multidisciplinary docking, kinetics and X-ray crystallography studies of baicalein acting as a glycogen phosphorylase inhibitor and determination of its' potential against glioblastoma in cellular models. Chem Biol Interact. 2023 Sep 1;382:110568. doi: 10.1016/j.cbi.2023.110568. Epub 2023 Jun 3.
13 The autonomous notch signal pathway is activated by baicalin and baicalein but is suppressed by niclosamide in K562 cells. J Cell Biochem. 2009 Mar 1;106(4):682-92. doi: 10.1002/jcb.22065.
14 MiR-3663-3p participates in the anti-hepatocellular carcinoma proliferation activity of baicalein by targeting SH3GL1 and negatively regulating EGFR/ERK/NF-B signaling. Toxicol Appl Pharmacol. 2021 Jun 1;420:115522. doi: 10.1016/j.taap.2021.115522. Epub 2021 Apr 8.