1,3-Bis(1,3-benzodioxol-5-yl)-3-hydroxy-2-propen-1-one

Details

• Internal ID: 37389f70-6ec5-4df0-bb67-330647ccf10d
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: (Z)-1,3-bis(1,3-benzodioxol-5-yl)-3-hydroxyprop-2-en-1-one
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C(=CC(=O)C3=CC4=C(C=C3)OCO4)O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)/C(=C/C(=O)C3=CC4=C(C=C3)OCO4)/O
• InChI: InChI=1S/C17H12O6/c18-12(10-1-3-14-16(5-10)22-8-20-14)7-13(19)11-2-4-15-17(6-11)23-9-21-15/h1-7,18H,8-9H2/b12-7-
• InChI Key: AFLGTFMAMFQGGU-GHXNOFRVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₆
• Molecular Weight: 312.27 g/mol
• Exact Mass: 312.06338810 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.93
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 1,3-Bis(1,3-benzodioxol-5-yl)-3-hydroxy-2-propen-1-one
• SCHEMBL10057828
• LMPK12120402

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.7359	73.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7048	70.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9563	95.63%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4797	47.97%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.9896	98.96%
CYP3A4 substrate	-	0.7275	72.75%
CYP2C9 substrate	-	0.8166	81.66%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	+	0.6905	69.05%
CYP2C9 inhibition	+	0.5116	51.16%
CYP2C19 inhibition	+	0.6097	60.97%
CYP2D6 inhibition	-	0.5906	59.06%
CYP1A2 inhibition	+	0.8287	82.87%
CYP2C8 inhibition	-	0.8865	88.65%
CYP inhibitory promiscuity	+	0.7691	76.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4436	44.36%
Eye corrosion	-	0.9774	97.74%
Eye irritation	+	0.9056	90.56%
Skin irritation	-	0.5454	54.54%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8542	85.42%
Micronuclear	+	0.7074	70.74%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6019	60.19%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.8800	88.00%
Androgen receptor binding	+	0.8041	80.41%
Thyroid receptor binding	+	0.7104	71.04%
Glucocorticoid receptor binding	+	0.5990	59.90%
Aromatase binding	+	0.5794	57.94%
PPAR gamma	+	0.8469	84.69%
Honey bee toxicity	-	0.9656	96.56%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7652	76.52%
Fish aquatic toxicity	+	0.9806	98.06%

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	95.32%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.83%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.78%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.52%	96.77%
CHEMBL4208	P20618	Proteasome component C5	90.46%	90.00%
CHEMBL2039	P27338	Monoamine oxidase B	87.71%	92.51%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.88%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.47%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.23%	99.17%

Plants that contains it

• Angostura granulosa

Cross-Links

• PubChem: 42607653
• LOTUS: LTS0236457
• wikiData: Q76535079