6-hydroxy-7-methoxy-3-(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-2-benzofuran-1-one

Details

• Internal ID: 3931aa29-2046-4c1d-80db-f6b2ebc8179b
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: 6-hydroxy-7-methoxy-3-(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-3H-2-benzofuran-1-one
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)O)OC)C(=O)O4)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)O)OC)C(=O)O4)OCO3
• InChI: InChI=1S/C20H19NO6/c1-21-6-5-10-7-14-15(26-9-25-14)8-12(10)17(21)18-11-3-4-13(22)19(24-2)16(11)20(23)27-18/h3-4,7-8,17-18,22H,5-6,9H2,1-2H3
• InChI Key: BXLGLBCDUIMUFL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.12123733 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9213	92.13%
Caco-2	+	0.7876	78.76%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4420	44.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9378	93.78%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6134	61.34%
P-glycoprotein inhibitior	+	0.6242	62.42%
P-glycoprotein substrate	-	0.8580	85.80%
CYP3A4 substrate	+	0.6415	64.15%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.6702	67.02%
CYP3A4 inhibition	+	0.7112	71.12%
CYP2C9 inhibition	+	0.7265	72.65%
CYP2C19 inhibition	+	0.7606	76.06%
CYP2D6 inhibition	-	0.8049	80.49%
CYP1A2 inhibition	-	0.7412	74.12%
CYP2C8 inhibition	-	0.8466	84.66%
CYP inhibitory promiscuity	-	0.5907	59.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5962	59.62%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9673	96.73%
Skin irritation	-	0.7898	78.98%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7074	70.74%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8674	86.74%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7731	77.31%
Acute Oral Toxicity (c)	III	0.7522	75.22%
Estrogen receptor binding	+	0.8240	82.40%
Androgen receptor binding	-	0.6000	60.00%
Thyroid receptor binding	-	0.6679	66.79%
Glucocorticoid receptor binding	+	0.8369	83.69%
Aromatase binding	-	0.5283	52.83%
PPAR gamma	+	0.8053	80.53%
Honey bee toxicity	-	0.8717	87.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7720	77.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.21%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.64%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.42%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.52%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.19%	93.99%
CHEMBL2581	P07339	Cathepsin D	92.81%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.70%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.72%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.35%	99.23%
CHEMBL2056	P21728	Dopamine D1 receptor	90.30%	91.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.93%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.33%	85.14%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.25%	80.78%
CHEMBL2535	P11166	Glucose transporter	87.58%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.31%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.18%	95.89%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.08%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.66%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.61%	94.00%
CHEMBL4208	P20618	Proteasome component C5	82.96%	90.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.23%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	81.54%	96.76%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.99%	82.38%

Plants that contains it

• Corydalis pseudoadunca

Cross-Links

• PubChem: 23266899
• LOTUS: LTS0003574
• wikiData: Q104948058