Details of the Drug

General Information of Drug (ID: DM2ZLD7)

• Drug Name: bisphenol A
• Synonyms: BPA

Indication

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

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 228.29
  Logarithm of the Partition Coefficient (xlogp); 3.3
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 2
• Chemical Identifiers:
  Formula: C15H16O2
  IUPAC Name: 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol
  Canonical SMILES: CC(C)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
  InChI: InChI=1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
  InChIKey: IISBACLAFKSPIT-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 6623
  ChEBI ID: CHEBI:33216
  CAS Number: 80-05-7
  DrugBank ID: DB06973
  TTD ID: D02RQP
  INTEDE ID: DR1984

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Androgen receptor messenger RNA (AR mRNA)	TTKPW01	ANDR_HUMAN	Antagonist	[2]
Estrogen receptor beta (ESR2)	TTOM3J0	ESR2_HUMAN	Agonist	[2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Sulfotransferase 2A1 (SULT2A1) Main DME	DE0P6LK	ST2A1_HUMAN	Substrate	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
(E3-independent) E2 ubiquitin-conjugating enzyme	OTHGS2VA	UBE2O_HUMAN	Gene/Protein Processing	[4]
(Lyso)-N-acylphosphatidylethanolamine lipase (ABHD4)	OTQK3M9X	ABHD4_HUMAN	Gene/Protein Processing	[5]
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1)	OTG2T749	CP24A_HUMAN	Gene/Protein Processing	[6]
1,4-alpha-glucan-branching enzyme (GBE1)	OTK2N05B	GLGB_HUMAN	Post-Translational Modifications	[7]
1,5-anhydro-D-fructose reductase (AKR1E2)	OT7GBQEB	AKCL2_HUMAN	Gene/Protein Processing	[8]
1-acyl-sn-glycerol-3-phosphate acyltransferase alpha (AGPAT1)	OTX65INE	PLCA_HUMAN	Gene/Protein Processing	[6]
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2)	OT5I4Y9K	PLCB_HUMAN	Gene/Protein Processing	[9]
1-acyl-sn-glycerol-3-phosphate acyltransferase delta (AGPAT4)	OT5CTQKO	PLCD_HUMAN	Gene/Protein Processing	[10]
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon (AGPAT5)	OTNY3VMD	PLCE_HUMAN	Post-Translational Modifications	[7]
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma (AGPAT3)	OTAUR5TG	PLCC_HUMAN	Post-Translational Modifications	[7]

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 receptor beta (ESR2)	DTT	ESR2	2.09E-01	-0.06	-0.17
Androgen receptor messenger RNA (AR mRNA)	DTT	AR	4.81E-01	-0.23	-0.29
Sulfotransferase 2A1 (SULT2A1)	DME	SULT2A1	2.90E-03	-2.24E-01	-1.19E+00

References

• [1] Antiandrogenic effects of bisphenol A and nonylphenol on the function of androgen receptor. Toxicol Sci. 2003 Sep;75(1):40-6.
• [2] Structure-activity relationships of bisphenol A analogs at estrogen receptors (ERs): discovery of an ERalpha-selective antagonist. Bioorg Med Chem Lett. 2013 Jul 15;23(14):4031-6.
• [3] Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
• [4] Environmental pollutant induced cellular injury is reflected in exosomes from placental explants. Placenta. 2020 Jan 1;89:42-49. doi: 10.1016/j.placenta.2019.10.008. Epub 2019 Oct 17.
• [5] Bisphenol A induces DSB-ATM-p53 signaling leading to cell cycle arrest, senescence, autophagy, stress response, and estrogen release in human fetal lung fibroblasts. Arch Toxicol. 2018 Apr;92(4):1453-1469.
• [6] Comprehensive analysis of transcriptomic changes induced by low and high doses of bisphenol A in HepG2 spheroids in vitro and rat liver in vivo. Environ Res. 2019 Jun;173:124-134. doi: 10.1016/j.envres.2019.03.035. Epub 2019 Mar 18.
• [7] DNA methylome-wide alterations associated with estrogen receptor-dependent effects of bisphenols in breast cancer. Clin Epigenetics. 2019 Oct 10;11(1):138. doi: 10.1186/s13148-019-0725-y.
• [8] Comparison of transcriptome expression alterations by chronic exposure to low-dose bisphenol A in different subtypes of breast cancer cells. Toxicol Appl Pharmacol. 2019 Dec 15;385:114814. doi: 10.1016/j.taap.2019.114814. Epub 2019 Nov 9.
• [9] Alternatives for the worse: Molecular insights into adverse effects of bisphenol a and substitutes during human adipocyte differentiation. Environ Int. 2021 Nov;156:106730. doi: 10.1016/j.envint.2021.106730. Epub 2021 Jun 27.
• [10] Identification of mechanisms of action of bisphenol a-induced human preadipocyte differentiation by transcriptional profiling. Obesity (Silver Spring). 2014 Nov;22(11):2333-43.