8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one

Details

• Internal ID: 31e93137-4dda-47de-a264-2c8f3f01ef86
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: [1,3]dioxolo[4,5-h]chromen-8-one
• SMILES (Canonical): C1OC2=C(O1)C3=C(C=C2)C=CC(=O)O3
• SMILES (Isomeric): C1OC2=C(O1)C3=C(C=C2)C=CC(=O)O3
• InChI: InChI=1S/C10H6O4/c11-8-4-2-6-1-3-7-10(9(6)14-8)13-5-12-7/h1-4H,5H2
• InChI Key: OZRUEXJYRHKIJC-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.15 g/mol
• Exact Mass: 190.02660867 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 7,8-Methylenedioxycoumarin
• 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one
• [1,3]dioxolo[4,5-h]chromen-8-one
• 1,3,9-Trioxa-cyclopenta[a]naphthalen-8-one
• CHEMBL611651
• SCHEMBL6778388
• CHEBI:173903
• DTXSID601035577
• MFCD25563368
• XM163701
• 2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one
• 2H,8H-[1,3]Dioxolo[4,5-h][1]benzopyran-8-one
• 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.8216	82.16%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6890	68.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9552	95.52%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8036	80.36%
P-glycoprotein inhibitior	-	0.9512	95.12%
P-glycoprotein substrate	-	0.9843	98.43%
CYP3A4 substrate	-	0.7188	71.88%
CYP2C9 substrate	-	0.8427	84.27%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	+	0.8108	81.08%
CYP2C9 inhibition	+	0.6232	62.32%
CYP2C19 inhibition	+	0.7383	73.83%
CYP2D6 inhibition	+	0.7389	73.89%
CYP1A2 inhibition	+	0.9053	90.53%
CYP2C8 inhibition	-	0.9620	96.20%
CYP inhibitory promiscuity	+	0.7229	72.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4927	49.27%
Eye corrosion	-	0.9583	95.83%
Eye irritation	+	0.9783	97.83%
Skin irritation	+	0.5252	52.52%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6828	68.28%
Micronuclear	+	0.7874	78.74%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.6041	60.41%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6860	68.60%
Acute Oral Toxicity (c)	III	0.5130	51.30%
Estrogen receptor binding	-	0.5648	56.48%
Androgen receptor binding	+	0.8165	81.65%
Thyroid receptor binding	-	0.6884	68.84%
Glucocorticoid receptor binding	-	0.6907	69.07%
Aromatase binding	+	0.6017	60.17%
PPAR gamma	+	0.5354	53.54%
Honey bee toxicity	-	0.8872	88.72%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9164	91.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	95.58%	85.30%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.91%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.82%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.49%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.80%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.12%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.43%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.45%	94.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.45%	86.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.64%	82.67%

Plants that contains it

• Artemisia dracunculus
• Diosma acmaephylla
• Pterocaulon polystachyum

Cross-Links

• PubChem: 13704003
• LOTUS: LTS0023737
• wikiData: Q105204070