4-([1,3]Dioxolo[4,5-g]isoquinolin-5-ylmethyl)phenol

Details

• Internal ID: 7aa9379c-83e0-4ecb-9b03-96fc73d42648
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 4-([1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)phenol
• SMILES (Canonical): C1OC2=C(O1)C=C3C(=C2)C=CN=C3CC4=CC=C(C=C4)O
• SMILES (Isomeric): C1OC2=C(O1)C=C3C(=C2)C=CN=C3CC4=CC=C(C=C4)O
• InChI: InChI=1S/C17H13NO3/c19-13-3-1-11(2-4-13)7-15-14-9-17-16(20-10-21-17)8-12(14)5-6-18-15/h1-6,8-9,19H,7,10H2
• InChI Key: KRHLIEJPAKUMIW-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.29 g/mol
• Exact Mass: 279.08954328 g/mol
• Topological Polar Surface Area (TPSA): 51.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.26
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 4-([1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)phenol
• phenol, 4-(1,3-dioxolo[4,5-g]isoquinolin-5-ylmethyl)-
• 1-(p-hydroxy-benzyl)-6,7-methylenedioxyisoquinoline
• 4-[1,3]Dioxolo[4,5-g]isoquinolin-5-ylmethyl-phenol
• InChI=1/C17H13NO3/c19-13-3-1-11(2-4-13)7-15-14-9-17-16(20-10-21-17)8-12(14)5-6-18-15/h1-6,8-9,19H,7,10H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.6449	64.49%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7253	72.53%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.8892	88.92%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7874	78.74%
P-glycoprotein inhibitior	-	0.7142	71.42%
P-glycoprotein substrate	-	0.6377	63.77%
CYP3A4 substrate	-	0.5731	57.31%
CYP2C9 substrate	-	0.8001	80.01%
CYP2D6 substrate	-	0.6835	68.35%
CYP3A4 inhibition	+	0.6554	65.54%
CYP2C9 inhibition	-	0.7485	74.85%
CYP2C19 inhibition	-	0.6771	67.71%
CYP2D6 inhibition	+	0.6960	69.60%
CYP1A2 inhibition	+	0.9210	92.10%
CYP2C8 inhibition	+	0.7728	77.28%
CYP inhibitory promiscuity	+	0.6330	63.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5595	55.95%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.6304	63.04%
Skin irritation	-	0.6508	65.08%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6563	65.63%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7347	73.47%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6576	65.76%
Acute Oral Toxicity (c)	III	0.5175	51.75%
Estrogen receptor binding	+	0.9162	91.62%
Androgen receptor binding	+	0.8378	83.78%
Thyroid receptor binding	+	0.8011	80.11%
Glucocorticoid receptor binding	+	0.8364	83.64%
Aromatase binding	+	0.9040	90.40%
PPAR gamma	+	0.9230	92.30%
Honey bee toxicity	-	0.8375	83.75%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.6118	61.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	97.82%	93.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.49%	91.49%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	92.87%	96.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.07%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.79%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.35%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.34%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.56%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.67%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.49%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.48%	99.15%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.45%	89.44%
CHEMBL2535	P11166	Glucose transporter	85.79%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	84.57%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.13%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.01%	89.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.27%	85.49%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.90%	95.78%
CHEMBL1952	P04818	Thymidylate synthase	80.90%	93.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.53%	95.89%

Plants that contains it

• Neolitsea acuminatissima

Cross-Links

• PubChem: 636843
• LOTUS: LTS0075964
• wikiData: Q105145013