3-[(2R,3S)-3-Ethyloxiran-2-yl]-1H-2-benzopyran-1-one

Details

• Internal ID: 10f6fc71-2750-4bef-a10a-35bcf8b59781
• Taxonomy: Phenylpropanoids and polyketides > Isocoumarins and derivatives
• IUPAC Name: 3-[(2R,3S)-3-ethyloxiran-2-yl]isochromen-1-one
• SMILES (Canonical): CCC1C(O1)C2=CC3=CC=CC=C3C(=O)O2
• SMILES (Isomeric): CC[C@H]1[C@@H](O1)C2=CC3=CC=CC=C3C(=O)O2
• InChI: InChI=1S/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1
• InChI Key: VNEONZFLGNRQJT-CMPLNLGQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.23 g/mol
• Exact Mass: 216.078644241 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• (?)-(R,S)-Epoxyartemidin
• 653597-74-1
• CHEMBL464936
• VNEONZFLGNRQJT-CMPLNLGQSA-
• DTXSID40616068
• 3-[(2R,3S)-3-Ethyloxiran-2-yl]-1H-2-benzopyran-1-one
• InChI=1/C13H12O3/c1-2-10-12(15-10)11-7-8-5-3-4-6-9(8)13(14)16-11/h3-7,10,12H,2H2,1H3/t10-,12+/m0/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.8276	82.76%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6662	66.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9034	90.34%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8100	81.00%
P-glycoprotein inhibitior	-	0.8607	86.07%
P-glycoprotein substrate	-	0.8962	89.62%
CYP3A4 substrate	-	0.5661	56.61%
CYP2C9 substrate	-	0.5890	58.90%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.8387	83.87%
CYP2C9 inhibition	-	0.6783	67.83%
CYP2C19 inhibition	-	0.6317	63.17%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	-	0.5751	57.51%
CYP2C8 inhibition	-	0.7857	78.57%
CYP inhibitory promiscuity	-	0.5411	54.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4637	46.37%
Eye corrosion	-	0.9750	97.50%
Eye irritation	-	0.6401	64.01%
Skin irritation	-	0.5707	57.07%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6251	62.51%
Micronuclear	+	0.6818	68.18%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.7442	74.42%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8125	81.25%
Acute Oral Toxicity (c)	III	0.5930	59.30%
Estrogen receptor binding	+	0.7160	71.60%
Androgen receptor binding	+	0.7026	70.26%
Thyroid receptor binding	-	0.5255	52.55%
Glucocorticoid receptor binding	-	0.6661	66.61%
Aromatase binding	-	0.4917	49.17%
PPAR gamma	-	0.5638	56.38%
Honey bee toxicity	-	0.9177	91.77%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8990	89.90%

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	97.69%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.17%	94.73%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.12%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.26%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.41%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.00%	93.65%

Plants that contains it

• Artemisia campestris
• Artemisia dracunculus

Cross-Links

• PubChem: 21580105
• NPASS: NPC308744
• LOTUS: LTS0055078
• wikiData: Q82517859