General Information of Drug (ID: DM7V2LG)

Drug Name
Chrysin
Synonyms
chrysin; 480-40-0; 5,7-Dihydroxyflavone; Chrysine; 5,7-Dihydroxy-2-phenyl-4H-chromen-4-one; Crysin; 5,7-dihydroxy-2-phenylchromen-4-one; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-phenyl-; UNII-3CN01F5ZJ5; NSC-407436; FLAVONE, 5,7-DIHYDROXY-; EINECS 207-549-7; NSC407436; 5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one; CHEMBL117; NSC 407436; 5,7-Dihydroxy-2-phenyl-chromen-4-one; BRN 0233276; 3CN01F5ZJ5; CHEBI:75095; RTIXKCRFFJGDFG-UHFFFAOYSA-N; 5,7-Dihydroxy-2-phenyl-4H-benzo(b)pyran-4-one; MFCD00006834; Chrysin, 99+%; CAS-480-40-0
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 254.24
Logarithm of the Partition Coefficient (xlogp) 2.1
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C15H10O4
IUPAC Name
5,7-dihydroxy-2-phenylchromen-4-one
Canonical SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
InChI
InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
InChIKey
RTIXKCRFFJGDFG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281607
ChEBI ID
CHEBI:75095
CAS Number
480-40-0
DrugBank ID
DB15581
TTD ID
D01UYI
VARIDT ID
DR01258
INTEDE ID
DR1939

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aldose reductase (AKR1B1) TTFBNVI ALDR_HUMAN Inhibitor [2]
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [3]
Cyclin-dependent kinase 6 (CDK6) TTO0FDJ CDK6_HUMAN Inhibitor [4]
Cytochrome P450 1B1 (CYP1B1) TTI84H7 CP1B1_HUMAN Inhibitor [1]
Plasmodium Oxoacyl-[acyl-carrier protein] reductase (Malaria fabG) TTBE4IR Q965D6_PLAFA Inhibitor [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [7]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [7]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DE2GB8N UD18_HUMAN Substrate [7]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DEZO4N3 UD17_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 (PLCG1) OTSBQR6D PLCG1_HUMAN Protein Interaction/Cellular Processes [8]
14-3-3 protein sigma (SFN) OTLJCZ1U 1433S_HUMAN Gene/Protein Processing [9]
6-phosphogluconate dehydrogenase, decarboxylating (PGD) OTVG296F 6PGD_HUMAN Gene/Protein Processing [10]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [11]
Acyl-CoA 6-desaturase (FADS2) OTUX531P FADS2_HUMAN Gene/Protein Processing [12]
Aldo-keto reductase family 1 member B10 (AKR1B10) OTOA4HTH AK1BA_HUMAN Gene/Protein Processing [13]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Drug Response [8]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [14]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [15]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Aldose reductase (AKR1B1) DTT AKR1B1 1.08E-20 0.94 1.58
Breast cancer resistance protein (ABCG2) DTP BCRP 1.07E-06 -3.94E-01 -6.94E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 1.04E-03 -7.68E-02 -3.85E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
2 Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin. Bioorg Med Chem. 2010 May 1;18(9):3020-5.
3 Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
4 Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin. J Med Chem. 2005 Feb 10;48(3):737-43.
5 Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
6 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.
7 Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. J Biol Chem. 2004 Jan 9;279(2):1429-41.
8 Bcl-2 attenuates anticancer agents-induced apoptosis by sustained activation of Akt/protein kinase B in U937 cells. Apoptosis. 2005 Dec;10(6):1333-43. doi: 10.1007/s10495-005-2763-5.
9 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.
10 Investigation of the effects of some phenolic compounds on the activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase from human erythrocytes. J Biochem Mol Toxicol. 2014 Nov;28(11):510-4. doi: 10.1002/jbt.21592. Epub 2014 Aug 6.
11 Chrysin inhibit human melanoma A375.S2 cell migration and invasion via affecting MAPK signaling and NF-B signaling pathway in vitro. Environ Toxicol. 2019 Apr;34(4):434-442. doi: 10.1002/tox.22697. Epub 2018 Dec 22.
12 Anti-inflammatory effects of dietary phenolic compounds in an in vitro model of inflamed human intestinal epithelium. Chem Biol Interact. 2010 Dec 5;188(3):659-67.
13 Chrysin enhances sensitivity of BEL-7402/ADM cells to doxorubicin by suppressing PI3K/Akt/Nrf2 and ERK/Nrf2 pathway. Chem Biol Interact. 2013 Oct 25;206(1):100-8.
14 Inhibition of aromatase activity by flavonoids. Arch Pharm Res. 1999 Jun;22(3):309-12.
15 Food flavonoid aryl hydrocarbon receptor-mediated agonistic/antagonistic/synergic activities in human and rat reporter gene assays. Anal Chim Acta. 2009 Apr 1;637(1-2):337-45. doi: 10.1016/j.aca.2008.09.054. Epub 2008 Oct 7.
16 Chrysin blocks topotecan-induced apoptosis in Caco-2 cells in spite of inhibition of ABC-transporters. Biochem Pharmacol. 2010 Aug 15;80(4):471-9. doi: 10.1016/j.bcp.2010.04.038. Epub 2010 May 8.