(S)-3-Ethyl-5,6,7-trimethoxyphthalide

Details

• Internal ID: 97459af1-ec82-49c0-8bba-3e028e271943
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Benzofuranones
• IUPAC Name: (3S)-3-ethyl-5,6,7-trimethoxy-3H-2-benzofuran-1-one
• SMILES (Canonical): CCC1C2=CC(=C(C(=C2C(=O)O1)OC)OC)OC
• SMILES (Isomeric): CC[C@H]1C2=CC(=C(C(=C2C(=O)O1)OC)OC)OC
• InChI: InChI=1S/C13H16O5/c1-5-8-7-6-9(15-2)11(16-3)12(17-4)10(7)13(14)18-8/h6,8H,5H2,1-4H3/t8-/m0/s1
• InChI Key: IFZFGLFEHCJCMD-QMMMGPOBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26 g/mol
• Exact Mass: 252.09977361 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.9082	90.82%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5992	59.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9006	90.06%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7733	77.33%
P-glycoprotein inhibitior	-	0.8458	84.58%
P-glycoprotein substrate	-	0.9226	92.26%
CYP3A4 substrate	-	0.5101	51.01%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8135	81.35%
CYP3A4 inhibition	-	0.8623	86.23%
CYP2C9 inhibition	-	0.7574	75.74%
CYP2C19 inhibition	+	0.7034	70.34%
CYP2D6 inhibition	-	0.9480	94.80%
CYP1A2 inhibition	+	0.8020	80.20%
CYP2C8 inhibition	+	0.4764	47.64%
CYP inhibitory promiscuity	+	0.6216	62.16%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5022	50.22%
Eye corrosion	-	0.9359	93.59%
Eye irritation	+	0.5547	55.47%
Skin irritation	-	0.8467	84.67%
Skin corrosion	-	0.9764	97.64%
Ames mutagenesis	-	0.6964	69.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4515	45.15%
Micronuclear	+	0.5477	54.77%
Hepatotoxicity	+	0.6177	61.77%
skin sensitisation	-	0.7012	70.12%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7092	70.92%
Acute Oral Toxicity (c)	II	0.3658	36.58%
Estrogen receptor binding	-	0.5272	52.72%
Androgen receptor binding	-	0.6588	65.88%
Thyroid receptor binding	+	0.6313	63.13%
Glucocorticoid receptor binding	-	0.6032	60.32%
Aromatase binding	-	0.7034	70.34%
PPAR gamma	-	0.5632	56.32%
Honey bee toxicity	-	0.8654	86.54%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8689	86.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.97%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.78%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.57%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.02%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.02%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.61%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.55%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.15%	92.62%
CHEMBL2535	P11166	Glucose transporter	84.44%	98.75%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.36%	94.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.67%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.99%	97.25%

Plants that contains it

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

Cross-Links

• PubChem: 25135574
• NPASS: NPC27106
• ChEMBL: CHEMBL450406
• LOTUS: LTS0131498
• wikiData: Q105112491