1-Phenyl-1,2-propanedione

Details

• Internal ID: cb891286-ab44-4995-91bd-c4779467fe48
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: 1-phenylpropane-1,2-dione
• SMILES (Canonical): CC(=O)C(=O)C1=CC=CC=C1
• SMILES (Isomeric): CC(=O)C(=O)C1=CC=CC=C1
• InChI: InChI=1S/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H3
• InChI Key: BVQVLAIMHVDZEL-UHFFFAOYSA-N
• Popularity: 214 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16 g/mol
• Exact Mass: 148.052429494 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 1-Phenylpropane-1,2-dione
• 579-07-7
• Acetylbenzoyl
• Acetyl benzoyl
• Benzoylacetyl
• 1,2-Propanedione, 1-phenyl-
• Pyruvophenone
• Methylphenylglyoxal
• Benzoyl methyl ketone
• Phenylmethyldiketone
• 3-Phenyl-2,3-propanedione
• Methyl phenyl diketone
• Methyl phenyl glyoxal
• Phenyl methyl diketone
• 1-Phenyl-propane-1,2-dione
• FEMA No. 3226
• 1-phenyl-1,2-propandione
• CCRIS 6297
• NSC 7643
• EINECS 209-435-2
• UNII-ZB5XA3GD0I
• MFCD00008755
• ZB5XA3GD0I
• AI3-23868
• CHEBI:63552
• NSC-7643
• phenyl-propane dione
• alpha-keto-propiophenone
• 2-OXOPROPIOPHENONE
• Phenyl-1,2-Propanedione
• D02TLP
• 1-phenyl-1,2-dioxopropane
• 1-phenyl-1,2-propane dione
• SCHEMBL180411
• CHEMBL192258
• Phenyl-1,2-propanedione, 1-
• SCHEMBL8670415
• DTXSID3060372
• BDBM22724
• FEMA 3226
• NSC7643
• 1-Phenyl-1,2-propanedione, 99%
• 1-PHENYL-2-OXOPROPAN-1-ONE
• s6009
• AKOS003382258
• CS-W019544
• HY-W018758
• 1-Phenyl-1,2-propanedione, 98%, FG
• AS-11744
• SY036428
• 1-PHENYL-1,2-PROPANEDIONE [FHFI]
• LS-179806
• AM20040761
• FT-0608215
• P0210
• EN300-98681
• C17268
• F11432
• A831668
• W-105429
• Q27132685
• Z1255485389
• InChI=1/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.7655	76.55%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8245	82.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9646	96.46%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8836	88.36%
P-glycoprotein inhibitior	-	0.9913	99.13%
P-glycoprotein substrate	-	0.9869	98.69%
CYP3A4 substrate	-	0.8013	80.13%
CYP2C9 substrate	-	0.8132	81.32%
CYP2D6 substrate	-	0.7818	78.18%
CYP3A4 inhibition	-	0.9739	97.39%
CYP2C9 inhibition	-	0.8969	89.69%
CYP2C19 inhibition	-	0.9057	90.57%
CYP2D6 inhibition	-	0.9522	95.22%
CYP1A2 inhibition	-	0.7271	72.71%
CYP2C8 inhibition	-	0.8733	87.33%
CYP inhibitory promiscuity	-	0.8907	89.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5410	54.10%
Carcinogenicity (trinary)	Non-required	0.6720	67.20%
Eye corrosion	+	0.9737	97.37%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.9236	92.36%
Skin corrosion	+	0.6378	63.78%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8656	86.56%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	+	0.9593	95.93%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.8222	82.22%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5143	51.43%
Acute Oral Toxicity (c)	III	0.8717	87.17%
Estrogen receptor binding	-	0.9453	94.53%
Androgen receptor binding	-	0.7868	78.68%
Thyroid receptor binding	-	0.8259	82.59%
Glucocorticoid receptor binding	-	0.9237	92.37%
Aromatase binding	-	0.9012	90.12%
PPAR gamma	-	0.9141	91.41%
Honey bee toxicity	-	0.9894	98.94%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4198	41.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	5270 nM; 5270 nM	Ki; Ki	PMID: 15828829; PMID: 21733699
CHEMBL3180	O00748	Carboxylesterase 2	1840 nM; 1840 nM	Ki; Ki	PMID: 15828829; PMID: 21733699

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	90.01%	90.17%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.86%	95.50%

Plants that contains it

• Cinnamomum aromaticum
• Ephedra equisetina
• Ephedra intermedia
• Ephedra sinica
• Styrax benzoin

Cross-Links

• PubChem: 11363
• NPASS: NPC300205
• ChEMBL: CHEMBL192258