4-Hydroxyphenylacetamide

Details

• Internal ID: f8f9faf3-d3d2-496a-9386-37235018a024
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylacetamides
• IUPAC Name: 2-(4-hydroxyphenyl)acetamide
• SMILES (Canonical): C1=CC(=CC=C1CC(=O)N)O
• SMILES (Isomeric): C1=CC(=CC=C1CC(=O)N)O
• InChI: InChI=1S/C8H9NO2/c9-8(11)5-6-1-3-7(10)4-2-6/h1-4,10H,5H2,(H2,9,11)
• InChI Key: YBPAYPRLUDCSEY-UHFFFAOYSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16 g/mol
• Exact Mass: 151.063328530 g/mol
• Topological Polar Surface Area (TPSA): 63.30 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 17194-82-0
• 2-(4-Hydroxyphenyl)acetamide
• p-Hydroxyphenylacetamide
• 4-Hydroxybenzeneacetamide
• Benzeneacetamide, 4-hydroxy-
• p-(Carbamoylmethyl)phenol
• (p-Hydroxyphenyl)acetamide
• 2-(p-Hydroxyphenyl)acetamide
• (4-Hydroxyphenyl)acetamide
• 4-(Hydroxyphenyl)acetamide
• Acetamide, 2-(p-hydroxyphenyl)-
• MFCD00017145
• p-Hydroxyphenyl acetamide
• 0HY0N4ITN4
• CHEMBL447310
• NSC-187193
• 4-hydroxy phenylacetamide
• EINECS 241-235-0
• UNII-0HY0N4ITN4
• BRN 2085984
• 2-(4-Hydroxyphenyl)-ethylamide
• 2-(4-Hydroxyphenyl)acetamide; Atenolol Imp. A (EP); Atenolol Impurity A
• P-Hydroxyphenyl-acetamide
• P-HYDROXY BENZYLAMIDE
• Oprea1_206241
• 3-10-00-00434 (Beilstein Handbook Reference)
• 4-Hydroxyphenylacetamide,(S)
• SCHEMBL661973
• 4-Hydroxyphenylacetamide, 99%
• alpha-(p-Hydroxyphenyl)acetamide
• DTXSID4066171
• YBPAYPRLUDCSEY-UHFFFAOYSA-
• CHEBI:194828
• HYDROXYPHENYLACETAMIDE, 4-
• BDBM50339587
• NSC187193
• AKOS005716492
• AC-6787
• CCG-356424
• CS-W016314
• NSC 187193
• PS-4609
• s12297
• SY001683
• FT-0618730
• FT-0618731
• H0853
• EN300-219225
• A811367
• W-107869
• 2-(4-hydroxyphenyl)acetamide;4-Hydroxyphenylacetamide
• Q27236794
• InChI=1/C8H9NO2/c9-8(11)5-6-1-3-7(10)4-2-6/h1-4,10H,5H2,(H2,9,11)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9523	95.23%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6378	63.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9410	94.10%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9137	91.37%
P-glycoprotein inhibitior	-	0.9919	99.19%
P-glycoprotein substrate	-	0.9619	96.19%
CYP3A4 substrate	-	0.7443	74.43%
CYP2C9 substrate	-	0.8185	81.85%
CYP2D6 substrate	-	0.7744	77.44%
CYP3A4 inhibition	-	0.8185	81.85%
CYP2C9 inhibition	-	0.9307	93.07%
CYP2C19 inhibition	-	0.8549	85.49%
CYP2D6 inhibition	-	0.9406	94.06%
CYP1A2 inhibition	-	0.9214	92.14%
CYP2C8 inhibition	-	0.8365	83.65%
CYP inhibitory promiscuity	-	0.8946	89.46%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.5945	59.45%
Carcinogenicity (trinary)	Non-required	0.5664	56.64%
Eye corrosion	-	0.9884	98.84%
Eye irritation	+	0.9543	95.43%
Skin irritation	-	0.6332	63.32%
Skin corrosion	-	0.9618	96.18%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8719	87.19%
Micronuclear	+	0.6685	66.85%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7384	73.84%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7369	73.69%
Acute Oral Toxicity (c)	III	0.7679	76.79%
Estrogen receptor binding	-	0.8896	88.96%
Androgen receptor binding	-	0.6246	62.46%
Thyroid receptor binding	-	0.7651	76.51%
Glucocorticoid receptor binding	-	0.7807	78.07%
Aromatase binding	-	0.7999	79.99%
PPAR gamma	-	0.5641	56.41%
Honey bee toxicity	-	0.9733	97.33%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.9397	93.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.23%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.72%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.38%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.25%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.53%	95.50%

Plants that contains it

• Bongardia chrysogonum
• Moringa oleifera

Cross-Links

• PubChem: 86986
• LOTUS: LTS0243835
• wikiData: Q27236794