5-[(1S)-4,5-dimethoxy-3-methylidene-1H-2-benzofuran-1-yl]-4-methoxy-6,9-dimethyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline

Details

• Internal ID: b1e1e37e-40e4-41e8-bcae-b093cb30dbe1
• Taxonomy: Organoheterocyclic compounds > Tetrahydroisoquinolines
• IUPAC Name: 5-[(1S)-4,5-dimethoxy-3-methylidene-1H-2-benzofuran-1-yl]-4-methoxy-6,9-dimethyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• SMILES (Canonical): CC1=C2CCN(C(C2=C(C3=C1OCO3)OC)C4C5=C(C(=C)O4)C(=C(C=C5)OC)OC)C
• SMILES (Isomeric): CC1=C2CCN(C(C2=C(C3=C1OCO3)OC)[C@@H]4C5=C(C(=C)O4)C(=C(C=C5)OC)OC)C
• InChI: InChI=1S/C24H27NO6/c1-12-14-9-10-25(3)19(18(14)23(28-6)24-20(12)29-11-30-24)21-15-7-8-16(26-4)22(27-5)17(15)13(2)31-21/h7-8,19,21H,2,9-11H2,1,3-6H3/t19?,21-/m0/s1
• InChI Key: YHIGEHDHOQLBHS-QWAKEFERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.50 g/mol
• Exact Mass: 425.18383758 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9088	90.88%
Caco-2	+	0.8225	82.25%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4042	40.42%
OATP2B1 inhibitior	-	0.8668	86.68%
OATP1B1 inhibitior	+	0.9322	93.22%
OATP1B3 inhibitior	+	0.9362	93.62%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8587	85.87%
P-glycoprotein inhibitior	+	0.8194	81.94%
P-glycoprotein substrate	-	0.7082	70.82%
CYP3A4 substrate	+	0.6606	66.06%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	+	0.5648	56.48%
CYP3A4 inhibition	+	0.8324	83.24%
CYP2C9 inhibition	+	0.5398	53.98%
CYP2C19 inhibition	+	0.5919	59.19%
CYP2D6 inhibition	-	0.6730	67.30%
CYP1A2 inhibition	-	0.7621	76.21%
CYP2C8 inhibition	+	0.5478	54.78%
CYP inhibitory promiscuity	+	0.6429	64.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4900	49.00%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9314	93.14%
Skin irritation	-	0.7733	77.33%
Skin corrosion	-	0.9288	92.88%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4210	42.10%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8385	83.85%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8409	84.09%
Acute Oral Toxicity (c)	III	0.6807	68.07%
Estrogen receptor binding	+	0.8218	82.18%
Androgen receptor binding	-	0.5910	59.10%
Thyroid receptor binding	+	0.6320	63.20%
Glucocorticoid receptor binding	+	0.7364	73.64%
Aromatase binding	+	0.5700	57.00%
PPAR gamma	+	0.6616	66.16%
Honey bee toxicity	-	0.8215	82.15%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9464	94.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.72%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.24%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.13%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.94%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.16%	94.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	90.02%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.41%	96.77%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.41%	82.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.24%	95.89%
CHEMBL2535	P11166	Glucose transporter	89.17%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	88.22%	82.38%
CHEMBL2056	P21728	Dopamine D1 receptor	86.24%	91.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.61%	89.62%
CHEMBL2581	P07339	Cathepsin D	83.59%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.46%	92.62%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	82.36%	95.71%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.32%	96.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.59%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.38%	100.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.04%	96.39%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	80.63%	98.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.46%	99.18%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.44%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.27%	99.23%

Plants that contains it

• Aquilaria malaccensis
• Papaver somniferum

Cross-Links

• PubChem: 5317792
• NPASS: NPC244300