Details of the Drug

General Information of Drug (ID: DMW9CH2)

• Drug Name: Tetramethylbutylphenol
• Synonyms: P-T-Octylphenol; Phenol, p-(tert-octyl)-; p-Octylphenol (VAN); p-Terc.oktylfenol; p-terc.Oktylfenol [Czech]; p-tert-Octylphenol; para-tert-Octylphenol; 4-(1,1,3,3-Tetramethylbutyl)phenol; tert-Octylphenol, flaked; 140-66-9; 4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL; 4-(2,4,4-trimethylpentan-2-yl)phenol; 4-(TERT-OCTYL)PHENOL; 4-t-Octylphenol; 4-tert-Octylphenol; BRN 0513992; EINECS 205-426-2; HSDB 5411; NSC 5427; Phenol, 4-(1,1,3,3-tetramethylbutyl)-; Phenol, p-(1,1,3,3-tetramethylbutyl)-; IOY9FVU3J3; UNII-IOY9FVU3J3; p-(1,1,3,3-Tetramethylbutyl)phenol
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 206.32
  Logarithm of the Partition Coefficient (xlogp); 5
  Rotatable Bond Count (rotbonds); 3
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 1
• Chemical Identifiers:
  Formula: C14H22O
  IUPAC Name: 4-(2,4,4-trimethylpentan-2-yl)phenol
  Canonical SMILES: CC(C)(C)CC(C)(C)C1=CC=C(C=C1)O
  InChI: ISAVYTVYFVQUDY-UHFFFAOYSA-N
  InChIKey: 1S/C14H22O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11/h6-9,15H,10H2,1-5H3
• Cross-matching ID:
  PubChem CID: 8814
  ChEBI ID: CHEBI:34445
  CAS Number: 140-66-9
  INTEDE ID: DR1983

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Sulfotransferase 2A1 (SULT2A1) Main DME	DE0P6LK	ST2A1_HUMAN	Substrate	[1]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[2]
Cadherin-1 (CDH1)	OTFJMXPM	CADH1_HUMAN	Gene/Protein Processing	[3]
Cadherin-2 (CDH2)	OTH0Y56P	CADH2_HUMAN	Gene/Protein Processing	[3]
Cathepsin B (CTSB)	OTP9G5QB	CATB_HUMAN	Gene/Protein Processing	[4]
Cathepsin D (CTSD)	OTQZ36F3	CATD_HUMAN	Gene/Protein Processing	[4]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Post-Translational Modifications	[5]
Cyclic AMP-responsive element-binding protein 1 (CREB1)	OT1MDLA1	CREB1_HUMAN	Post-Translational Modifications	[5]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[6]
Cyclin-dependent kinase inhibitor 1B (CDKN1B)	OTNY5LLZ	CDN1B_HUMAN	Post-Translational Modifications	[5]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Drug Response	[7]

References

• [1] Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
• [2] Development and pre-validation of an in vitro transactivation assay for detection of (anti)androgenic potential compounds using 22Rv1/MMTV cells. Reprod Toxicol. 2016 Apr;60:156-66. doi: 10.1016/j.reprotox.2016.02.006. Epub 2016 Feb 8.
• [3] Effect of benzophenone-1 and octylphenol on the regulation of epithelial-mesenchymal transition via an estrogen receptor-dependent pathway in estrogen receptor expressing ovarian cancer cells. Food Chem Toxicol. 2016 Jul;93:58-65. doi: 10.1016/j.fct.2016.04.026. Epub 2016 May 1.
• [4] 4-tert-Octylphenol stimulates the expression of cathepsins in human breast cancer cells and xenografted breast tumors of a mouse model via an estrogen receptor-mediated signaling pathway. Toxicology. 2013 Feb 8;304:13-20. doi: 10.1016/j.tox.2012.10.012. Epub 2012 Dec 3.
• [5] Oncogenic Potential of Bisphenol A and Common Environmental Contaminants in Human Mammary Epithelial Cells. Int J Mol Sci. 2020 May 25;21(10):3735. doi: 10.3390/ijms21103735.
• [6] Progression of breast cancer cells was enhanced by endocrine-disrupting chemicals, triclosan and octylphenol, via an estrogen receptor-dependent signaling pathway in cellular and mouse xenograft models. Chem Res Toxicol. 2014 May 19;27(5):834-42. doi: 10.1021/tx5000156. Epub 2014 Apr 8.
• [7] Interactions between urinary 4-tert-octylphenol levels and metabolism enzyme gene variants on idiopathic male infertility. PLoS One. 2013;8(3):e59398. doi: 10.1371/journal.pone.0059398. Epub 2013 Mar 15.