p-Hydroxybenzalacetone

Details

• Internal ID: 31afe321-1c03-4a47-bfa2-bdc265a576fd
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (E)-4-(4-hydroxyphenyl)but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC1=CC=C(C=C1)O
• SMILES (Isomeric): CC(=O)/C=C/C1=CC=C(C=C1)O
• InChI: InChI=1S/C10H10O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h2-7,12H,1H3/b3-2+
• InChI Key: OCNIKEFATSKIBE-NSCUHMNNSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.18 g/mol
• Exact Mass: 162.068079557 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• p-Hydroxybenzalacetone
• 4-hydroxybenzylideneacetone
• 4-(4-Hydroxyphenyl)but-3-en-2-one
• 4-Hydroxybenzalacetone
• 4-Hydroxybenzal acetone
• 4-Hydroxycinnamoylmethane
• p-Hydroxybenzylidene acetone
• 4-(p-Hydroxyphenyl)-3-buten-2-one
• (E)-4-(4-hydroxyphenyl)but-3-en-2-one
• 22214-30-8
• p-hydroxyphenylbut-3-ene-2-one
• 3-Buten-2-one, 4-(4-hydroxyphenyl)-
• 3-Buten-2-one, 4-(p-hydroxyphenyl)-
• NSC 26516
• 4-Hydroxystyryl methyl ketone
• 1-(4-Hydroxybenzylidene)acetone
• EINECS 221-607-9
• (E)-4-(4-Hydroxyphenyl)-3-buten-2-one
• AI3-30539
• AI3-35956
• (3E)-4-(4-hydroxyphenyl)but-3-en-2-one
• (~{E})-4-(4-hydroxyphenyl)but-3-en-2-one
• 3-Buten-2-one, 4-(4-hydroxyphenyl)-, (E)-
• MFCD00016490
• 4-Hydroxybenzylidene acetone
• CHEMBL9184
• SCHEMBL807859
• p-hydroxyphenylbut-3ene-2-one
• Methyl P-Hydroxycinnamyl Ketone
• DTXSID2062878
• CHEBI:68636
• DTXSID201287493
• CS-B1377
• NSC26516
• NSC-26516
• STL506899
• AKOS005207153
• AS-61561
• 4-(4'-hydroxyphenyl)-(e)-3-buten-2-one
• CS-0356795
• 3-Buten-2-one,4-(4-hydroxyphenyl)-,(3E)-
• EN300-1858559
• J-018486
• Q27137063
• 8MK

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8536	85.36%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8089	80.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9772	97.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8052	80.52%
P-glycoprotein inhibitior	-	0.9849	98.49%
P-glycoprotein substrate	-	0.9687	96.87%
CYP3A4 substrate	-	0.6906	69.06%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8281	82.81%
CYP3A4 inhibition	-	0.7894	78.94%
CYP2C9 inhibition	-	0.9441	94.41%
CYP2C19 inhibition	-	0.8120	81.20%
CYP2D6 inhibition	-	0.9666	96.66%
CYP1A2 inhibition	-	0.5135	51.35%
CYP2C8 inhibition	-	0.7772	77.72%
CYP inhibitory promiscuity	-	0.8290	82.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5832	58.32%
Carcinogenicity (trinary)	Non-required	0.6225	62.25%
Eye corrosion	+	0.9449	94.49%
Eye irritation	+	0.9970	99.70%
Skin irritation	+	0.9295	92.95%
Skin corrosion	+	0.6823	68.23%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8170	81.70%
Micronuclear	+	0.5040	50.40%
Hepatotoxicity	-	0.5721	57.21%
skin sensitisation	+	0.9399	93.99%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.9250	92.50%
Nephrotoxicity	+	0.6479	64.79%
Acute Oral Toxicity (c)	III	0.8046	80.46%
Estrogen receptor binding	-	0.7659	76.59%
Androgen receptor binding	-	0.4825	48.25%
Thyroid receptor binding	-	0.8396	83.96%
Glucocorticoid receptor binding	-	0.7534	75.34%
Aromatase binding	-	0.7130	71.30%
PPAR gamma	-	0.8046	80.46%
Honey bee toxicity	-	0.9613	96.13%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8454	84.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.65%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.43%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.13%	96.00%
CHEMBL2581	P07339	Cathepsin D	84.16%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.99%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.61%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.33%	93.10%
CHEMBL242	Q92731	Estrogen receptor beta	83.11%	98.35%
CHEMBL3401	O75469	Pregnane X receptor	80.14%	94.73%

Plants that contains it

• Alpinia roxburghii
• Phlomis bovei
• Scutellaria barbata

Cross-Links

• PubChem: 796857
• NPASS: NPC181709
• LOTUS: LTS0224221
• wikiData: Q105189467