Details of the Drug

General Information of Drug (ID: DMI3491)

Drug Name
APIGENIN
Synonyms
apigenin; 520-36-5; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; Chamomile; Versulin; Spigenin; Apigenol; 4',5,7-Trihydroxyflavone; Apigenine; C.I. Natural Yellow 1; 5,7,4'-Trihydroxyflavone; Pelargidenon 1449; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone; 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone; UCCF 031; NSC 83244; UNII-7V515PI7F6; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; CCRIS 3789; CHEBI:18388; CHEMBL28; EINECS 208-292-3; 4H-1-Benzopyran-4-one, 5,7-di
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) 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
5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Canonical SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChIKey
KZNIFHPLKGYRTM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5280443
ChEBI ID
CHEBI:18388
CAS Number
520-36-5
DrugBank ID
DB07352
TTD ID
D00RIX
VARIDT ID
DR00822

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]
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Inhibitor [3]
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [4]
Casein kinase II alpha (CSNK2A1) TTER6YH CSK21_HUMAN Inhibitor [5]
Cyclin-dependent kinase 6 (CDK6) TTO0FDJ CDK6_HUMAN Inhibitor [6]
Cytochrome P450 1B1 (CYP1B1) TTI84H7 CP1B1_HUMAN Inhibitor [7]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1) TTIWB6L DHB1_HUMAN Inhibitor [8]
Influenza Neuraminidase (Influ NA) TT50QJ3 NRAM_I33A0 Inhibitor [9]
Plasmodium CDK Pfmrk (Malaria Pfmrk) TTSFWA7 P90584_PLAFA Inhibitor [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [11]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [12]
Baculoviral IAP repeat-containing protein 3 (BIRC3) OT3E95KB BIRC3_HUMAN Protein Interaction/Cellular Processes [11]
Beta-1,3-galactosyltransferase 5 (B3GALT5) OTWXPEMU B3GT5_HUMAN Gene/Protein Processing [13]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [14]
Caspase-7 (CASP7) OTAPJ040 CASP7_HUMAN Gene/Protein Processing [15]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Protein Interaction/Cellular Processes [11]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Protein Interaction/Cellular Processes [11]
Catalase (CAT) OTHEBX9R CATA_HUMAN Gene/Protein Processing [16]
CCN family member 5 (CCN5) OTADU8JJ CCN5_HUMAN Gene/Protein Processing [17]
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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 4136).
2 Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity. J Nat Prod. 2008 Apr;71(4):713-5.
3 Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10.
4 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.
5 Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid. Bioorg Med Chem Lett. 2009 Jun 1;19(11):2920-3.
6 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.
7 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
8 Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. J Med Chem. 2008 Jul 24;51(14):4188-99.
9 Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities. Bioorg Med Chem. 2009 Oct 1;17(19):6816-23.
10 A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different class... J Med Chem. 2004 Oct 21;47(22):5418-26.
11 Apigenin drives the production of reactive oxygen species and initiates a mitochondrial mediated cell death pathway in prostate epithelial cells. Prostate. 2005 May 1;63(2):131-42. doi: 10.1002/pros.20167.
12 Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):216-25. doi: 10.1016/j.jsbmb.2006.06.021. Epub 2006 Sep 11.
13 Differential responses to retinoic acid and endocrine disruptor compounds of subpopulations within human embryonic stem cell lines. Differentiation. 2012 Nov;84(4):330-43. doi: 10.1016/j.diff.2012.07.006. Epub 2012 Aug 18.
14 Apigenin suppresses cancer cell growth through ERbeta. Neoplasia. 2006 Nov;8(11):896-904. doi: 10.1593/neo.06538.
15 Apigenin-induced apoptosis is mediated by reactive oxygen species and activation of ERK1/2 in rheumatoid fibroblast-like synoviocytes. Chem Biol Interact. 2009 Nov 10;182(1):29-36. doi: 10.1016/j.cbi.2009.07.016. Epub 2009 Aug 6.
16 Involvement of catalase in the apoptotic mechanism induced by apigenin in HepG2 human hepatoma cells. Chem Biol Interact. 2011 Sep 5;193(2):180-9.
17 Endocrine-Disrupting Chemicals (EDCs): In Vitro Mechanism of Estrogenic Activation and Differential Effects on ER Target Genes. Environ Health Perspect. 2013 Apr;121(4):459-66. doi: 10.1289/ehp.1205951. Epub 2013 Feb 5.