6-(6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-E][1,3]benzodioxol-8(6H)-one

Details

• Internal ID: 591a9cc3-84a2-4fe8-b1b3-305986f3c9e5
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: 6-(6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3,4-g][1,3]benzodioxol-8-one
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
• InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3
• InChI Key: IYGYMKDQCDOMRE-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₇NO₆
• Molecular Weight: 367.40 g/mol
• Exact Mass: 367.10558726 g/mol
• Topological Polar Surface Area (TPSA): 66.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
• Oprea1_485116
• 6-(6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-E][1,3]benzodioxol-8(6H)-one
• SCHEMBL5481014
• CHEMBL1444722
• ACon1_001600
• DTXSID30859402
• IYGYMKDQCDOMRE-UHFFFAOYSA-N
• (+)-Bicuculline,1(S),9(R)
• HMS3369C12
• Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-
• AKOS003404630
• AKOS022144165
• NCGC00015169-02
• NCGC00015169-03
• NCGC00017385-02
• NCGC00017385-03
• NCGC00142541-01
• NCGC00142541-02
• 6-(6-Methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2H-furo[3,4-e][1,3]benzodioxol-8(6H)-one
• 6-(6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-E][1,3]benzodioxol-8(6H)-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	+	0.7738	77.38%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4400	44.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.9409	94.09%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8511	85.11%
P-glycoprotein inhibitior	-	0.6282	62.82%
P-glycoprotein substrate	-	0.8209	82.09%
CYP3A4 substrate	+	0.6019	60.19%
CYP2C9 substrate	+	0.8024	80.24%
CYP2D6 substrate	-	0.6799	67.99%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.7664	76.64%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.6229	62.29%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9319	93.19%
CYP inhibitory promiscuity	-	0.5366	53.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5613	56.13%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9577	95.77%
Skin irritation	-	0.7658	76.58%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4086	40.86%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8574	85.74%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6036	60.36%
Acute Oral Toxicity (c)	III	0.7155	71.55%
Estrogen receptor binding	+	0.8442	84.42%
Androgen receptor binding	-	0.5329	53.29%
Thyroid receptor binding	-	0.7445	74.45%
Glucocorticoid receptor binding	+	0.8982	89.82%
Aromatase binding	+	0.5375	53.75%
PPAR gamma	+	0.7847	78.47%
Honey bee toxicity	-	0.8638	86.38%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.7800	78.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	281.8 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	98.56%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.00%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.48%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.51%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.39%	94.45%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	86.21%	81.29%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.00%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.76%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.45%	99.23%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.73%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.33%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	84.27%	91.00%
CHEMBL3384	Q16512	Protein kinase N1	83.70%	80.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.54%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.62%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.30%	89.00%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	80.60%	95.71%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.57%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.50%	92.62%

Plants that contains it

• Adlumia fungosa
• Corydalis caseana
• Corydalis cava
• Corydalis chaerophylla
• Corydalis govaniana
• Corydalis incisa
• Corydalis intermedia
• Corydalis nobilis
• Corydalis pseudoadunca
• Corydalis saxicola
• Corydalis scouleri
• Corydalis stricta
• Corydalis taliensis
• Dicentra cucullaria
• Fumaria parviflora
• Fumaria vaillantii

Cross-Links

• PubChem: 2376
• LOTUS: LTS0225363
• wikiData: Q105122740