Cycloisobrachycoumarinone Epoxide

Details

• Internal ID: 20ba71d6-5861-446f-9611-3784d1ff184d
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Angular furanocoumarins
• IUPAC Name: (2R,3S)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]-2-oxoethyl]-2,3,9-trimethyl-2H-furo[3,2-c]chromen-4-one
• InChI: InChI=1S/C20H22O5/c1-10-7-6-8-13-14(10)16-15(18(22)24-13)20(5,11(2)23-16)9-12(21)17-19(3,4)25-17/h6-8,11,17H,9H2,1-5H3/t11-,17+,20-/m1/s1
• InChI Key: QMWJPFXMOOPDTD-CGQHOMIXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• CIBC epoxide
• RefChem:129741
• (2R,3S)-3-(2-((2R)-3,3-dimethyloxiran-2-yl)-2-oxoethyl)-2,3,9-trimethyl-2H-furo(3,2-c)chromen-4-one
• 190062-46-5
• CHEMBL517042

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.7790	77.90%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6558	65.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9131	91.31%
P-glycoprotein inhibitior	-	0.5339	53.39%
P-glycoprotein substrate	-	0.6276	62.76%
CYP3A4 substrate	+	0.6128	61.28%
CYP2C9 substrate	-	0.5964	59.64%
CYP2D6 substrate	-	0.8419	84.19%
CYP3A4 inhibition	-	0.6196	61.96%
CYP2C9 inhibition	-	0.6848	68.48%
CYP2C19 inhibition	-	0.6480	64.80%
CYP2D6 inhibition	-	0.9152	91.52%
CYP1A2 inhibition	-	0.6334	63.34%
CYP2C8 inhibition	-	0.6433	64.33%
CYP inhibitory promiscuity	-	0.7999	79.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5027	50.27%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9422	94.22%
Skin irritation	-	0.7303	73.03%
Skin corrosion	-	0.8846	88.46%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6031	60.31%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.7149	71.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7110	71.10%
Acute Oral Toxicity (c)	III	0.5380	53.80%
Estrogen receptor binding	+	0.9130	91.30%
Androgen receptor binding	+	0.6303	63.03%
Thyroid receptor binding	+	0.5597	55.97%
Glucocorticoid receptor binding	+	0.6916	69.16%
Aromatase binding	+	0.5998	59.98%
PPAR gamma	+	0.8014	80.14%
Honey bee toxicity	-	0.9100	91.00%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9914	99.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.74%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.60%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.51%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.29%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.91%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.89%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.53%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.11%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.08%	94.80%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44566635
• LOTUS: LTS0087944
• wikiData: Q105224202