Dibenzoylmethane

Details

• Internal ID: e0b705a2-c407-4f4e-80b4-00dc66a2c1eb
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retro-dihydrochalcones
• IUPAC Name: 1,3-diphenylpropane-1,3-dione
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=CC=C2
• InChI: InChI=1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2
• InChI Key: NZZIMKJIVMHWJC-UHFFFAOYSA-N
• Popularity: 1,412 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.25 g/mol
• Exact Mass: 224.083729621 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 120-46-7
• 1,3-Diphenylpropane-1,3-dione
• 1,3-DIPHENYL-1,3-PROPANEDIONE
• 1,3-Propanedione, 1,3-diphenyl-
• 2-Benzoylacetophenone
• Phenyl phenacyl ketone
• Rhodiastab 83
• omega-Benzoylacetophenone
• Dibenzoyl-methane
• Karenzu DK2
• dibenzoyl methane
• 1,3-Diphenyl-propane-1,3-dione
• .omega.-Benzoylacetophenone
• NSC 6266
• MFCD00003085
• .gamma.-hydroxychalkone
• ANS7ME8OKC
• UNII-ANS7ME8OKC
• NSC-6266
• EINECS 204-398-9
• BRN 0514910
• AI3-19022
• CCRIS 8445
• DTXSID3041247
• CHEBI:75417
• EC 204-398-9
• Karenzu DK 2
• Karenz DK 2
• 1, 1,3-diphenyl-
• Spectrum2_000038
• Spectrum3_001950
• D02BDL
• SCHEMBL39582
• BSPBio_003550
• DIBENZOYLMETHANE [MI]
• MLS002695996
• SPECTRUM1505311
• SPBio_000135
• CHEMBL371523
• 1,3-diphenyl-1,3-propandione
• 1,3-diphenyl-1,3-propanedion
• DIBENZOYLMETHANE [MART.]
• DTXCID1021247
• phenyl-alpha-hydroxystyryl ketone
• 1 3-Diphenyl-1 3-propanedione
• BDBM22727
• KBio3_002841
• NSC6266
• 1,3-Diphenyl-Propan-1,3-Dion
• HMS3091A20
• 1,3-propanodiona, 1,3-difenil-
• STR01439
• Tox21_300686
• AC7872
• AD 158
• CCG-40047
• NSC 52984
• STK372683
• AKOS000119639
• CS-W010447
• HY-W009731
• NSC 406806
• 1,3-Diphenyl-1,3-propanedione, 98%
• UPCMLD0ENAT5883819:001
• NCGC00095298-01
• NCGC00095298-02
• NCGC00095298-03
• NCGC00095298-04
• NCGC00254594-01
• AC-11379
• CAS-120-46-7
• SMR001253722
• SY014045
• PHENYL-.ALPHA.-HYDROXYSTYRYL KETONE
• DIPHENYL-1,3-PROPANEDIONE, 1,3-
• LS-120771
• AM20020283
• D0910
• FT-0624640
• PROPANE-1,3-DIONE, 1,3-DIPHENYL-
• EN300-20083
• Dibenzoylmethane 1,3-Diphenyl-1,3-propanedione
• Q5272260
• W-108476
• BRD-K01555864-001-02-8
• Dibenzoylmethane (chronic inflammatory disease/cancer)
• F0001-0329
• Z104476748

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.8496	84.96%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7714	77.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9695	96.95%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5932	59.32%
P-glycoprotein inhibitior	-	0.9621	96.21%
P-glycoprotein substrate	-	0.9811	98.11%
CYP3A4 substrate	-	0.8421	84.21%
CYP2C9 substrate	-	0.7818	78.18%
CYP2D6 substrate	-	0.7129	71.29%
CYP3A4 inhibition	-	0.8353	83.53%
CYP2C9 inhibition	-	0.5175	51.75%
CYP2C19 inhibition	+	0.7590	75.90%
CYP2D6 inhibition	-	0.8577	85.77%
CYP1A2 inhibition	+	0.7852	78.52%
CYP2C8 inhibition	-	0.9166	91.66%
CYP inhibitory promiscuity	+	0.6137	61.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5113	51.13%
Carcinogenicity (trinary)	Non-required	0.6992	69.92%
Eye corrosion	-	0.5932	59.32%
Eye irritation	+	0.9819	98.19%
Skin irritation	+	0.6457	64.57%
Skin corrosion	-	0.7489	74.89%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6627	66.27%
Micronuclear	-	0.7715	77.15%
Hepatotoxicity	+	0.6927	69.27%
skin sensitisation	+	0.6150	61.50%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.8333	83.33%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5859	58.59%
Estrogen receptor binding	+	0.7357	73.57%
Androgen receptor binding	-	0.6366	63.66%
Thyroid receptor binding	-	0.7334	73.34%
Glucocorticoid receptor binding	-	0.7637	76.37%
Aromatase binding	+	0.8403	84.03%
PPAR gamma	+	0.5568	55.68%
Honey bee toxicity	-	0.9759	97.59%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8032	80.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	39810.7 nM	Potency	via CMAUP
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	26000 nM	Ki	PMID: 15828829
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	10000 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	6309.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	12589.3 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	96.77%	90.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	87.41%	81.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.37%	87.67%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.57%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.43%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.63%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.86%	99.17%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis

Cross-Links

• PubChem: 8433
• NPASS: NPC273758
• ChEMBL: CHEMBL371523