Details of the Drug

General Information of Drug (ID: DM0HPWY)

Drug Name

biochanin A

Synonyms

Biochanin A; 491-80-5; Biochanin; 4'-Methylgenistein; 5,7-Dihydroxy-4'-methoxyisoflavone; 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one; Genistein 4-methyl ether; 5,7-Dihydrox -4'-methoxyisoflavone; Biochanine A; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-; olmelin; Pratensol; NSC 123538; Biochanin-A; 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one; 4-Methylgenistein; C16H12O5; UNII-U13J6U390T; CCRIS 5449; 5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one; EINECS 207-744-7; NSC123538; Genistein 4'-methyl ether; 4'-methylgenistein; BIOCHANIN

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

284.26

Logarithm of the Partition Coefficient (xlogp)

3

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

5

Chemical Identifiers

Formula: C16H12O5
IUPAC Name: 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
InChI: InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
InChIKey: WUADCCWRTIWANL-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5280373
ChEBI ID: CHEBI:17574
CAS Number: 491-80-5
DrugBank ID: DB15334
TTD ID: D0S9YX

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Aromatase (CYP19A1)	TTSZLWK	CP19A_HUMAN	Inhibitor	[2]
Estrogen-related receptor-alpha (ESRRA)	TTPNQAC	ERR1_HUMAN	Agonist	[3]
Estrogen-related receptor-beta (ESRRB)	TTKF0XS	ERR2_HUMAN	Agonist	[3]
Estrogen-related receptor-gamma (ESRRG)	TT9ZRHB	ERR3_HUMAN	Agonist	[3]
Fatty acid synthase (FASN)	TT7AOUD	FAS_HUMAN	Inhibitor	[4]
Plasmodium Beta-hydroxyacyl-ACP dehydratase (Malaria FabZ)	TTHPFTS	Q965D7_PLAFA	Inhibitor	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial (CYP27B1)	OTTK98BH	CP27B_HUMAN	Gene/Protein Processing	[5]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[6]
Agrin (AGRN)	OTWJENAZ	AGRIN_HUMAN	Gene/Protein Processing	[7]
Alpha-aminoadipic semialdehyde dehydrogenase (ALDH7A1)	OTV57BZD	AL7A1_HUMAN	Gene/Protein Processing	[7]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[8]
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[9]
Aryl hydrocarbon receptor (AHR)	OTFE4EYE	AHR_HUMAN	Gene/Protein Processing	[10]
AT-rich interactive domain-containing protein 5B (ARID5B)	OTUQ4CQY	ARI5B_HUMAN	Gene/Protein Processing	[7]
Bcl-2-like protein 1 (BCL2L1)	OTRC5K9O	B2CL1_HUMAN	Gene/Protein Processing	[8]
BRISC and BRCA1-A complex member 2 (BABAM2)	OTOY7FNT	BABA2_HUMAN	Gene/Protein Processing	[7]

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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

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Estrogen-related receptor-alpha (ESRRA)	DTT	ESRRA	9.34E-01	1.47E-02	0.06
Estrogen-related receptor-alpha (ESRRA)	DTT	ESRRA	2.09E-01	-0.07	-0.62

Molecular Expression Atlas (MEA)

MEA Detail

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: 2829).
2	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.
3	Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91.
4	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.
5	25-Hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds. Circulation. 2005 Apr 5;111(13):1666-71.
6	Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones. J Neurooncol. 2006 Sep;79(2):135-42. doi: 10.1007/s11060-006-9126-0. Epub 2006 Apr 6.
7	Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts. Prostate. 2002 Aug 1;52(3):201-12.
8	Effects of soy isoflavones on apoptosis induction and G2-M arrest in human hepatoma cells involvement of caspase-3 activation, Bcl-2 and Bcl-XL downregulation, and Cdc2 kinase activity. Nutr Cancer. 2003;45(1):113-23. doi: 10.1207/S15327914NC4501_13.
9	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.
10	Red clover aryl hydrocarbon receptor (AhR) and estrogen receptor (ER) agonists enhance genotoxic estrogen metabolism. Chem Res Toxicol. 2017 Nov 20;30(11):2084-2092.