Benzoylacetone

Details

• Internal ID: eb5794ef-0215-4f44-8b28-4b926e4e8b6c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 1-phenylbutane-1,3-dione
• SMILES (Canonical): CC(=O)CC(=O)C1=CC=CC=C1
• SMILES (Isomeric): CC(=O)CC(=O)C1=CC=CC=C1
• InChI: InChI=1S/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H3
• InChI Key: CVBUKMMMRLOKQR-UHFFFAOYSA-N
• Popularity: 1,073 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): 34.10 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 93-91-4
• 1-PHENYL-1,3-BUTANEDIONE
• 1-Phenylbutane-1,3-dione
• 1-Benzoylacetone
• 1,3-Butanedione, 1-phenyl-
• Acetoacetophenone
• Acetylbenzoylmethane
• 1-Benzoyl-2-propanone
• 2-Propanone, benzoyl-
• 2-Acetylacetophenone
• Benzoyl-aceton
• benzoyl acetone
• alpha-Acetylacetophenone
• .alpha.-Acetylacetophenone
• 1-phenyl-butane-1,3-dione
• MFCD00008786
• Benzoyl-aceton [German]
• NSC 4015
• AI3-10572
• EINECS 202-286-4
• BRN 0742413
• UNII-I3RUV8U115
• I3RUV8U115
• DTXSID3021803
• NSC-4015
• NSC-100655
• 4-07-00-02151 (Beilstein Handbook Reference)
• NSC-83580
• NSC-83581
• NSC-87898
• NSC-88942
• NSC-97232
• NSC-97233
• NSC-404283
• NSC-405722
• NSC-405723
• NSC-405724
• 1-phenyl-1,3-butandione
• acetyl acetophenone
• 1-phenylbutan-1,3-dione
• 1-phenyl-butane-1,3 dione
• SCHEMBL15116
• DTXCID901803
• CHEMBL3186793
• NSC4015
• 4-PHENYL-2,4-BUTANEDIONE
• 1-Phenyl-1,3-butanedione, 99%
• STR01075
• 4-OXO-4-PHENYLBUTAN-2-ONE
• Tox21_202879
• NSC100655
• STK802149
• AKOS000119529
• PHENYL-1,3-BUTANEDIONE, 1-
• CS-W014323
• PS-3611
• CAS-93-91-4
• NCGC00260425-01
• LS-45895
• SY011141
• 1-METHYL-3-PHENYL-1,3-PROPANEDIONE
• FT-0622746
• EN300-19842
• B-0690
• A844735
• J-802021
• 1-Phenyl-1,3-butanedione, purum, >=98.0% (GC)
• Q27280358
• F3098-2657
• (Z)-4-hydroxy-4-phenyl-but-3-en-2-one;1-Phenyl-1,3-butanedione
• InChI=1/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.7229	72.29%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7515	75.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9509	95.09%
OATP1B3 inhibitior	+	0.9731	97.31%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8273	82.73%
P-glycoprotein inhibitior	-	0.9896	98.96%
P-glycoprotein substrate	-	0.9390	93.90%
CYP3A4 substrate	-	0.7882	78.82%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7541	75.41%
CYP3A4 inhibition	-	0.8855	88.55%
CYP2C9 inhibition	-	0.8643	86.43%
CYP2C19 inhibition	-	0.7654	76.54%
CYP2D6 inhibition	-	0.9013	90.13%
CYP1A2 inhibition	+	0.5243	52.43%
CYP2C8 inhibition	-	0.9356	93.56%
CYP inhibitory promiscuity	-	0.8483	84.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5294	52.94%
Carcinogenicity (trinary)	Non-required	0.6743	67.43%
Eye corrosion	+	0.9028	90.28%
Eye irritation	+	0.9626	96.26%
Skin irritation	+	0.8432	84.32%
Skin corrosion	-	0.5434	54.34%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8024	80.24%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	+	0.6672	66.72%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	+	0.5520	55.20%
Acute Oral Toxicity (c)	III	0.6508	65.08%
Estrogen receptor binding	-	0.9538	95.38%
Androgen receptor binding	-	0.8897	88.97%
Thyroid receptor binding	-	0.9034	90.34%
Glucocorticoid receptor binding	-	0.9170	91.70%
Aromatase binding	-	0.8513	85.13%
PPAR gamma	-	0.8409	84.09%
Honey bee toxicity	-	0.9804	98.04%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.6482	64.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	94.81%	90.17%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.19%	87.67%
CHEMBL2581	P07339	Cathepsin D	85.97%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.92%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.77%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.66%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.17%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.64%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.27%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.95%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.77%	91.11%

Plants that contains it

• Schisandra chinensis
• Scutellaria baicalensis

Cross-Links

• PubChem: 7166
• NPASS: NPC164086