(Z)-3-Ethylidene-7-hydroxy-6-methoxyphthalide

Details

• Internal ID: 7fe85f24-08d5-404f-aa18-bfff961d23dc
• Taxonomy: Organoheterocyclic compounds > Isocoumarans > Isobenzofuranones
• IUPAC Name: (3Z)-3-ethylidene-7-hydroxy-6-methoxy-2-benzofuran-1-one
• SMILES (Canonical): CC=C1C2=C(C(=C(C=C2)OC)O)C(=O)O1
• SMILES (Isomeric): C/C=C\1/C2=C(C(=C(C=C2)OC)O)C(=O)O1
• InChI: InChI=1S/C11H10O4/c1-3-7-6-4-5-8(14-2)10(12)9(6)11(13)15-7/h3-5,12H,1-2H3/b7-3-
• InChI Key: YCVXJZRPLHJINO-CLTKARDFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19 g/mol
• Exact Mass: 206.05790880 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (3Z)-3-Ethylidene-6-methoxy-7-hydroxyisobenzofuran-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9937	99.37%
Caco-2	+	0.8122	81.22%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6806	68.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8074	80.74%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8763	87.63%
P-glycoprotein inhibitior	-	0.9403	94.03%
P-glycoprotein substrate	-	0.9311	93.11%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5744	57.44%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.6220	62.20%
CYP2C9 inhibition	-	0.8660	86.60%
CYP2C19 inhibition	+	0.7162	71.62%
CYP2D6 inhibition	-	0.8918	89.18%
CYP1A2 inhibition	+	0.7245	72.45%
CYP2C8 inhibition	-	0.5716	57.16%
CYP inhibitory promiscuity	+	0.6910	69.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9140	91.40%
Carcinogenicity (trinary)	Danger	0.4010	40.10%
Eye corrosion	-	0.9132	91.32%
Eye irritation	+	0.9403	94.03%
Skin irritation	-	0.5981	59.81%
Skin corrosion	-	0.9740	97.40%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6900	69.00%
Micronuclear	+	0.8259	82.59%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6552	65.52%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6030	60.30%
Acute Oral Toxicity (c)	II	0.6120	61.20%
Estrogen receptor binding	+	0.7223	72.23%
Androgen receptor binding	+	0.5451	54.51%
Thyroid receptor binding	-	0.5894	58.94%
Glucocorticoid receptor binding	-	0.7247	72.47%
Aromatase binding	-	0.5467	54.67%
PPAR gamma	-	0.5510	55.10%
Honey bee toxicity	-	0.9343	93.43%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9578	95.78%

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	95.53%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.20%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.96%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.29%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.92%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.02%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.39%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	83.50%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	83.09%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.19%	96.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.12%	98.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.67%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.22%	90.00%
CHEMBL2535	P11166	Glucose transporter	80.18%	98.75%

Plants that contains it

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

Cross-Links

• PubChem: 25135576
• NPASS: NPC258307
• ChEMBL: CHEMBL487289
• LOTUS: LTS0241679
• wikiData: Q105346538