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: CHEMBL28
CAS Number: 520-36-5
UNII: FGL3685T2X
DrugBank ID: DB14357
TTD ID: D00RIX
VARIDT ID: DR00822

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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
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	[12]
CCN family member 5 (CCN5)	OTADU8JJ	CCN5_HUMAN	Gene/Protein Processing	[13]
Cyclin-dependent kinase 4 inhibitor C (CDKN2C)	OTCLOV90	CDN2C_HUMAN	Gene/Protein Processing	[14]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[15]
Cytochrome c (CYCS)	OTBFALJD	CYC_HUMAN	Protein Interaction/Cellular Processes	[11]
Dehydrogenase/reductase SDR family member 11 (DHRS11)	OTU3J0ZL	DHR11_HUMAN	Gene/Protein Processing	[16]
Glycophorin-A (GYPA)	OTABU4YV	GLPA_HUMAN	Gene/Protein Processing	[17]
Hepatocyte growth factor receptor (MET)	OT7K55MU	MET_HUMAN	Post-Translational Modifications	[18]
Homeobox protein NANOG (NANOG)	OTUEY1FM	NANOG_HUMAN	Gene/Protein Processing	[18]

Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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	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.
13	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.
14	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.
15	Cytotoxicity of flavones and flavonols to a human esophageal squamous cell carcinoma cell line (KYSE-510) by induction of G2/M arrest and apoptosis. Toxicol In Vitro. 2009 Aug;23(5):797-807. doi: 10.1016/j.tiv.2009.04.007. Epub 2009 May 3.
16	Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.
17	Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells. Chem Biol Interact. 2014 Sep 5;220:269-77. doi: 10.1016/j.cbi.2014.07.006. Epub 2014 Jul 21.
18	Apigenin Inhibits Cancer Stem Cell-Like Phenotypes in Human Glioblastoma Cells via Suppression of c-Met Signaling. Phytother Res. 2016 Nov;30(11):1833-1840. doi: 10.1002/ptr.5689. Epub 2016 Jul 29.