(3S)-3-Ethyl-5,6-dimethoxy-7-hydroxyisobenzofuran-1(3H)-one

Details

• Internal ID: 64f1a8b7-6727-4f18-9aee-0bf1072ca815
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Benzofuranones
• IUPAC Name: (3S)-3-ethyl-7-hydroxy-5,6-dimethoxy-3H-2-benzofuran-1-one
• SMILES (Canonical): CCC1C2=CC(=C(C(=C2C(=O)O1)O)OC)OC
• SMILES (Isomeric): CC[C@H]1C2=CC(=C(C(=C2C(=O)O1)O)OC)OC
• InChI: InChI=1S/C12H14O5/c1-4-7-6-5-8(15-2)11(16-3)10(13)9(6)12(14)17-7/h5,7,13H,4H2,1-3H3/t7-/m0/s1
• InChI Key: XQERYNXDLZZXIC-ZETCQYMHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24 g/mol
• Exact Mass: 238.08412354 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• (3S)-3-Ethyl-5,6-dimethoxy-7-hydroxyisobenzofuran-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	+	0.8659	86.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6547	65.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8522	85.22%
OATP1B3 inhibitior	+	0.9127	91.27%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8235	82.35%
P-glycoprotein inhibitior	-	0.8917	89.17%
P-glycoprotein substrate	-	0.9269	92.69%
CYP3A4 substrate	+	0.5092	50.92%
CYP2C9 substrate	+	0.6383	63.83%
CYP2D6 substrate	-	0.8234	82.34%
CYP3A4 inhibition	-	0.8969	89.69%
CYP2C9 inhibition	-	0.7736	77.36%
CYP2C19 inhibition	+	0.5105	51.05%
CYP2D6 inhibition	-	0.9453	94.53%
CYP1A2 inhibition	+	0.6262	62.62%
CYP2C8 inhibition	+	0.6739	67.39%
CYP inhibitory promiscuity	-	0.6481	64.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4946	49.46%
Eye corrosion	-	0.9577	95.77%
Eye irritation	+	0.5743	57.43%
Skin irritation	-	0.7910	79.10%
Skin corrosion	-	0.9729	97.29%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5377	53.77%
Micronuclear	+	0.6077	60.77%
Hepatotoxicity	-	0.5020	50.20%
skin sensitisation	-	0.7346	73.46%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8228	82.28%
Acute Oral Toxicity (c)	II	0.4716	47.16%
Estrogen receptor binding	+	0.5419	54.19%
Androgen receptor binding	-	0.6708	67.08%
Thyroid receptor binding	+	0.6040	60.40%
Glucocorticoid receptor binding	-	0.5066	50.66%
Aromatase binding	-	0.6925	69.25%
PPAR gamma	+	0.5671	56.71%
Honey bee toxicity	-	0.9054	90.54%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.8202	82.02%

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	97.95%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.84%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.11%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.72%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.21%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.24%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.92%	94.00%
CHEMBL2581	P07339	Cathepsin D	85.71%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.25%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.23%	94.45%
CHEMBL2535	P11166	Glucose transporter	80.34%	98.75%

Plants that contains it

• Chamaemelum fuscatum
• Citrullus colocynthis
• Onychium japonicum
• Pittosporum illicioides

Cross-Links

• PubChem: 25135573
• NPASS: NPC96501
• ChEMBL: CHEMBL408147
• LOTUS: LTS0070155
• wikiData: Q105339652