(2S)-10-hydroxy-2-prop-1-en-2-yl-2,3-dihydropyrano[2,3-g][1,4]benzodioxin-7-one

Details

• Internal ID: e513721b-4938-4198-a82c-ceb420964e29
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > p-Dioxolo[2,3-g]coumarins
• IUPAC Name: (2S)-10-hydroxy-2-prop-1-en-2-yl-2,3-dihydropyrano[2,3-g][1,4]benzodioxin-7-one
• SMILES (Canonical): CC(=C)C1COC2=C(O1)C(=C3C=CC(=O)OC3=C2)O
• SMILES (Isomeric): CC(=C)[C@H]1COC2=C(O1)C(=C3C=CC(=O)OC3=C2)O
• InChI: InChI=1S/C14H12O5/c1-7(2)11-6-17-10-5-9-8(3-4-12(15)18-9)13(16)14(10)19-11/h3-5,11,16H,1,6H2,2H3/t11-/m1/s1
• InChI Key: AVCYTMYLWMIAER-LLVKDONJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.7060	70.60%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7332	73.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8941	89.41%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6393	63.93%
P-glycoprotein inhibitior	-	0.7749	77.49%
P-glycoprotein substrate	-	0.6533	65.33%
CYP3A4 substrate	+	0.5054	50.54%
CYP2C9 substrate	-	0.6607	66.07%
CYP2D6 substrate	-	0.8336	83.36%
CYP3A4 inhibition	-	0.6979	69.79%
CYP2C9 inhibition	-	0.6871	68.71%
CYP2C19 inhibition	+	0.5199	51.99%
CYP2D6 inhibition	-	0.8366	83.66%
CYP1A2 inhibition	+	0.6951	69.51%
CYP2C8 inhibition	-	0.8015	80.15%
CYP inhibitory promiscuity	-	0.6446	64.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6955	69.55%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.6270	62.70%
Skin irritation	-	0.6589	65.89%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6657	66.57%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.6112	61.12%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8988	89.88%
Acute Oral Toxicity (c)	II	0.3974	39.74%
Estrogen receptor binding	+	0.8653	86.53%
Androgen receptor binding	+	0.8011	80.11%
Thyroid receptor binding	-	0.4914	49.14%
Glucocorticoid receptor binding	+	0.6582	65.82%
Aromatase binding	+	0.7000	70.00%
PPAR gamma	+	0.7233	72.33%
Honey bee toxicity	-	0.8110	81.10%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9796	97.96%

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	99.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	94.65%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.30%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.83%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.61%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.87%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.11%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.55%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.87%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	83.78%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.24%	94.00%

Plants that contains it

• Cassinia uncata
• Ozothamnus diosmifolius
• Plecostachys serpyllifolia
• Podolepis rugata

Cross-Links

• PubChem: 101244671
• LOTUS: LTS0276299
• wikiData: Q104919364