Details of the Drug

General Information of Drug (ID: DMH3OUX)

Drug Name
N-nonylphenol
Synonyms
Nonylphenol (mixed); Phenol, 4-nonyl-; Phenol, nonyl derivs.; Phenol, p-nonyl-; p -n -Nonylphenol; p-Nonylphenol; p-n-Nonylphenol; p-nonyl phenol; 4-N-nonylphenol; para Nonyl phenol; para-Nonylphenol; 1-(4-Hydroxyphenyl)nonane; 104-40-5; 4-NP; 4-Nonyl Phenol-13C6; 4-Nonyl-Phenol; 4-n-Nonyl phenol; 4-n-Nonylphenol; 4-nonyl phenol; 4-nonylphenol; 68081-86-7; BRN 2047450; CCRIS 1251; CHEBI:34440; DSSTox_CID_1857; IGFHQQFPSIBGKE-UHFFFAOYSA-N; DSSTox_GSID_33836; DSSTox_RID_79098; EINECS 203-199-4; HSDB 5359; MFCD00002396; P-NONYLPHENOL (ENDOCRINE DISRUPTER)
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 220.35
Logarithm of the Partition Coefficient (xlogp) 5.9
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 1
Chemical Identifiers
Formula
C15H24O
IUPAC Name
4-nonylphenol
Canonical SMILES
CCCCCCCCCC1=CC=C(C=C1)O
InChI
InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3
InChIKey
IGFHQQFPSIBGKE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1752
ChEBI ID
CHEMBL153062
CAS Number
104-40-5
INTEDE ID
DR1985
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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
Beta-1,4-galactosyltransferase 1 (B4GALT1) OTBCXEK7 B4GT1_HUMAN Gene/Protein Processing [2]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [3]
CCN family member 5 (CCN5) OTADU8JJ CCN5_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1C (CDKN1C) OTASTJ3Q CDN1C_HUMAN Gene/Protein Processing [6]
Early estrogen-induced gene 1 protein (EEIG1) OT2BMEAE EEIG1_HUMAN Gene/Protein Processing [2]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Post-Translational Modifications [7]
Lysosome-associated membrane glycoprotein 3 (LAMP3) OTN0XL3W LAMP3_HUMAN Gene/Protein Processing [8]
Na(+)/H(+) exchange regulatory cofactor NHE-RF3 (PDZK1) OTGFK4MH NHRF3_HUMAN Gene/Protein Processing [2]
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References

1 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
2 Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1. Mol Endocrinol. 2004 Feb;18(2):402-11. doi: 10.1210/me.2003-0202. Epub 2003 Nov 6.
3 The xenoestrogens, bisphenol A and para-nonylphenol, decrease the expression of the ABCG2 transporter protein in human term placental explant cultures. Mol Cell Endocrinol. 2016 Jul 5;429:41-9. doi: 10.1016/j.mce.2016.03.034. Epub 2016 Mar 30.
4 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.
5 Influence of hexabromocyclododecane and 4-nonylphenol on the regulation of cell growth, apoptosis and migration in prostatic cancer cells. Toxicol In Vitro. 2016 Apr;32:240-7. doi: 10.1016/j.tiv.2016.01.008. Epub 2016 Jan 19.
6 Low concentrations of Bisphenol A and para-Nonylphenol affect extravillous pathway of human trophoblast cells. Mol Cell Endocrinol. 2015 Sep 5;412:56-64. doi: 10.1016/j.mce.2015.05.023. Epub 2015 May 28.
7 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.
8 Epigenetic influences of low-dose bisphenol A in primary human breast epithelial cells. Toxicol Appl Pharmacol. 2010 Oct 15;248(2):111-21.