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

Details

• Internal ID: fb76789f-d35c-4395-996b-5ac1f8f51606
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 4-hydroxy-[1,3]dioxolo[4,5-h]chromen-8-one
• SMILES (Canonical): C1OC2=C(C=C3C=CC(=O)OC3=C2O1)O
• SMILES (Isomeric): C1OC2=C(C=C3C=CC(=O)OC3=C2O1)O
• InChI: InChI=1S/C10H6O5/c11-6-3-5-1-2-7(12)15-8(5)10-9(6)13-4-14-10/h1-3,11H,4H2
• InChI Key: BKFIQORTLXDLHQ-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆O₅
• Molecular Weight: 206.15 g/mol
• Exact Mass: 206.02152329 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 334007-19-1
• 8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one, 4-hydroxy-
• 4-hydroxy-[1,3]dioxolo[4,5-h]chromen-8-one
• DTXSID90469703
• MFCD24445522
• 6-hydroxy-7,8-methylenedioxy coumarin
• AKOS027326382
• 4-Hydroxy-8H-[1,3]dioxolo[4,5-h]chromen-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9698	96.98%
Caco-2	+	0.7209	72.09%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7581	75.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9515	95.15%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7585	75.85%
P-glycoprotein inhibitior	-	0.9356	93.56%
P-glycoprotein substrate	-	0.9829	98.29%
CYP3A4 substrate	-	0.7320	73.20%
CYP2C9 substrate	-	0.8173	81.73%
CYP2D6 substrate	-	0.8530	85.30%
CYP3A4 inhibition	+	0.6222	62.22%
CYP2C9 inhibition	+	0.5688	56.88%
CYP2C19 inhibition	-	0.5542	55.42%
CYP2D6 inhibition	+	0.5106	51.06%
CYP1A2 inhibition	+	0.7893	78.93%
CYP2C8 inhibition	-	0.9374	93.74%
CYP inhibitory promiscuity	-	0.5493	54.93%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4838	48.38%
Eye corrosion	-	0.9819	98.19%
Eye irritation	+	0.9874	98.74%
Skin irritation	-	0.5329	53.29%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7229	72.29%
Micronuclear	+	0.8174	81.74%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7462	74.62%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6061	60.61%
Acute Oral Toxicity (c)	II	0.4581	45.81%
Estrogen receptor binding	+	0.6311	63.11%
Androgen receptor binding	+	0.7309	73.09%
Thyroid receptor binding	-	0.5228	52.28%
Glucocorticoid receptor binding	-	0.5788	57.88%
Aromatase binding	-	0.4945	49.45%
PPAR gamma	+	0.7591	75.91%
Honey bee toxicity	-	0.9405	94.05%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8858	88.58%

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	98.18%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.80%	83.57%
CHEMBL2581	P07339	Cathepsin D	86.45%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.12%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.99%	85.30%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.91%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	81.67%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.61%	90.00%

Plants that contains it

• Artemisia capillaris

Cross-Links

• PubChem: 11629819
• LOTUS: LTS0118964
• wikiData: Q82297534