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

Details

• Internal ID: f919b4a5-d72f-4c48-aac3-268cb391c02c
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: (3S)-6,7-dimethoxy-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)OC)OC)C(=O)O4)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
• InChI: InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18?,19-/m0/s1
• InChI Key: JZUTXVTYJDCMDU-GGYWPGCISA-N
• Popularity: 54 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁NO₆
• Molecular Weight: 383.40 g/mol
• Exact Mass: 383.13688739 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• NSC646664
• CHEMBL462731
• NSC-646664
• NCGC00017326-02
• NCGC00142421-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9365	93.65%
Caco-2	+	0.8938	89.38%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4432	44.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9440	94.40%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9072	90.72%
P-glycoprotein inhibitior	+	0.9389	93.89%
P-glycoprotein substrate	-	0.8695	86.95%
CYP3A4 substrate	+	0.6520	65.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3512	35.12%
CYP3A4 inhibition	+	0.8035	80.35%
CYP2C9 inhibition	+	0.8950	89.50%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9007	90.07%
CYP2C8 inhibition	-	0.8187	81.87%
CYP inhibitory promiscuity	+	0.5827	58.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5569	55.69%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9666	96.66%
Skin irritation	-	0.7997	79.97%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4275	42.75%
Micronuclear	+	0.5274	52.74%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6766	67.66%
Acute Oral Toxicity (c)	III	0.7536	75.36%
Estrogen receptor binding	+	0.8500	85.00%
Androgen receptor binding	-	0.6370	63.70%
Thyroid receptor binding	-	0.7194	71.94%
Glucocorticoid receptor binding	+	0.8867	88.67%
Aromatase binding	-	0.6557	65.57%
PPAR gamma	+	0.7753	77.53%
Honey bee toxicity	-	0.8331	83.31%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8141	81.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	3.2 nM	Potency	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	0.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.59%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.18%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.07%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.29%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.61%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.54%	86.33%
CHEMBL261	P00915	Carbonic anhydrase I	92.60%	96.76%
CHEMBL2581	P07339	Cathepsin D	90.83%	98.95%
CHEMBL2056	P21728	Dopamine D1 receptor	90.05%	91.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.50%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.17%	95.89%
CHEMBL2535	P11166	Glucose transporter	88.95%	98.75%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	88.90%	96.86%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.70%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.40%	92.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.81%	82.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.48%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.34%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.66%	99.23%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	84.89%	100.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.87%	90.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.03%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.38%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.28%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.94%	97.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.12%	95.78%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.06%	92.38%

Plants that contains it

• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Hydrastis canadensis

Cross-Links

• PubChem: 371942
• NPASS: NPC14622
• ChEMBL: CHEMBL462731
• LOTUS: LTS0244703
• wikiData: Q105137598