4-Nonylphenol

Details

• Internal ID: fbe085da-8224-40ae-8528-7e9c5c915458
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: 4-nonylphenol
• SMILES (Canonical): CCCCCCCCCC1=CC=C(C=C1)O
• SMILES (Isomeric): 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
• InChI Key: IGFHQQFPSIBGKE-UHFFFAOYSA-N
• Popularity: 2,259 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35 g/mol
• Exact Mass: 220.182715385 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.69
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• 4-n-Nonylphenol
• 104-40-5
• p-Nonylphenol
• para-Nonylphenol
• Phenol, 4-nonyl-
• p-n-Nonylphenol
• 4-nonyl phenol
• Phenol, p-nonyl-
• para Nonyl phenol
• p -n -Nonylphenol
• 4-Nonyl Phenol-13C6
• 4-Nonyl-Phenol
• 4-n-Nonyl phenol
• CCRIS 1251
• DTXSID5033836
• HSDB 5359
• EINECS 203-199-4
• UNII-I03GBV4WEL
• BRN 2047450
• CHEBI:34440
• 4-Nonylphenol-2,3,5,6-d4
• MFCD00002396
• P-NONYLPHENOL (ENDOCRINE DISRUPTER)
• 4-N-NONYLPHENOL-2,3,5,6-D4,OD
• 3-06-00-02067 (Beilstein Handbook Reference)
• 68081-86-7
• 4-NP
• DTXCID001857
• CAS-104-40-5
• 358730-95-7
• nonyl-phenol
• p-nonyl phenol
• p-nonyl-phenol
• Para-nonyl phenol
• Nonylphenol, 4-
• Nonyl phenol, p-
• Fenol, 4-nonil-
• 4-Nonylphenol, tech.
• Spectrum_001973
• NONYLPHENOL, P-
• SpecPlus_000624
• Spectrum2_001832
• Spectrum3_000872
• Spectrum4_000712
• Spectrum5_002066
• 4-Nonylphenol (4-NP)
• I03GBV4WEL
• BIDD:PXR0002
• SCHEMBL15887
• BSPBio_002543
• KBioGR_001263
• KBioSS_002539
• SPECTRUM330085
• BIDD:ER0006
• DivK1c_006720
• SPBio_001903
• CHEMBL153062
• KBio1_001664
• KBio2_002530
• KBio2_005098
• KBio2_007666
• KBio3_002043
• 4-Nonylphenol, analytical standard
• EINECS 268-359-8
• Tox21_201241
• Tox21_303647
• BDBM50410532
• CCG-39613
• LMPK15010001
• LS-375
• STL453644
• AKOS015888197
• NCGC00090918-01
• NCGC00090918-02
• NCGC00090918-03
• NCGC00090918-05
• NCGC00090918-06
• NCGC00090918-07
• NCGC00090918-08
• NCGC00257420-01
• NCGC00258793-01
• PD002549
• FT-0619310
• FT-0673035
• 4-n-Nonylphenol 10 microg/mL in Acetonitrile
• 4-n-Nonylphenol 10 microg/mL in Cyclohexane
• 4-n-Nonylphenol 100 microg/mL in Cyclohexane
• 4-Nonylphenol, PESTANAL(R), analytical standard
• SR-05000002459
• J-001167
• Q4545806
• SR-05000002459-1
• 4-Nonylphenol, certified reference material, TraceCERT(R)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9504	95.04%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6118	61.18%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.7955	79.55%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7269	72.69%
P-glycoprotein inhibitior	-	0.9315	93.15%
P-glycoprotein substrate	-	0.6476	64.76%
CYP3A4 substrate	-	0.6226	62.26%
CYP2C9 substrate	-	0.7842	78.42%
CYP2D6 substrate	+	0.4159	41.59%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8374	83.74%
CYP2C19 inhibition	-	0.7490	74.90%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	+	0.6205	62.05%
CYP2C8 inhibition	+	0.7398	73.98%
CYP inhibitory promiscuity	-	0.6925	69.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7211	72.11%
Carcinogenicity (trinary)	Non-required	0.6492	64.92%
Eye corrosion	+	0.9827	98.27%
Eye irritation	+	0.9913	99.13%
Skin irritation	+	0.7967	79.67%
Skin corrosion	+	0.9671	96.71%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6610	66.10%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.5349	53.49%
skin sensitisation	+	0.9334	93.34%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	+	0.5362	53.62%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	-	0.5942	59.42%
Acute Oral Toxicity (c)	III	0.9253	92.53%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6290	62.90%
Thyroid receptor binding	+	0.6808	68.08%
Glucocorticoid receptor binding	-	0.8495	84.95%
Aromatase binding	-	0.5594	55.94%
PPAR gamma	+	0.8638	86.38%
Honey bee toxicity	-	0.9881	98.81%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.8411	84.11%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	1915 nM	IC50	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	100000 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	6780 nM	IC50	via CMAUP
CHEMBL246	P13945	Beta-3 adrenergic receptor	4190 nM	IC50	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL238	Q01959	Dopamine transporter	1649 nM	IC50	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL206	P03372	Estrogen receptor alpha	377 nM	IC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL2327	P21452	Neurokinin 2 receptor	4514 nM	IC50	via CMAUP
CHEMBL222	P23975	Norepinephrine transporter	1254 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 nM	Potency	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	2571 nM	IC50	via CMAUP
CHEMBL228	P31645	Serotonin transporter	3380 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.68%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.97%	92.08%
CHEMBL242	Q92731	Estrogen receptor beta	93.85%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.62%	96.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.44%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.05%	99.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.89%	92.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.30%	97.29%
CHEMBL2996	Q05655	Protein kinase C delta	86.33%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.77%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.55%	86.33%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	84.54%	94.01%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.33%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.65%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.61%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.00%	96.95%

Plants that contains it

• Schisandra chinensis

Cross-Links

• PubChem: 1752
• NPASS: NPC123273
• ChEMBL: CHEMBL153062