(5S)-5-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-4-ol

Details

• Internal ID: 751afd47-8d3d-41fa-ad79-51f6fe557282
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: (5S)-5-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-4-ol
• SMILES (Canonical): CN1CCC2=CC3=C(C(=C2C1CC4=CC(=C(C=C4)OC)O)O)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C(=C2[C@@H]1CC4=CC(=C(C=C4)OC)O)O)OCO3
• InChI: InChI=1S/C19H21NO5/c1-20-6-5-12-9-16-19(25-10-24-16)18(22)17(12)13(20)7-11-3-4-15(23-2)14(21)8-11/h3-4,8-9,13,21-22H,5-7,10H2,1-2H3/t13-/m0/s1
• InChI Key: NBEREFJAHQPIOC-ZDUSSCGKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.40 g/mol
• Exact Mass: 343.14197277 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6910	69.10%
Caco-2	+	0.8145	81.45%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4570	45.70%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.9315	93.15%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7750	77.50%
P-glycoprotein inhibitior	-	0.7937	79.37%
P-glycoprotein substrate	-	0.5521	55.21%
CYP3A4 substrate	+	0.6313	63.13%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6924	69.24%
CYP3A4 inhibition	-	0.7085	70.85%
CYP2C9 inhibition	-	0.8793	87.93%
CYP2C19 inhibition	-	0.5975	59.75%
CYP2D6 inhibition	-	0.5172	51.72%
CYP1A2 inhibition	-	0.6049	60.49%
CYP2C8 inhibition	-	0.6206	62.06%
CYP inhibitory promiscuity	-	0.6440	64.40%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9765	97.65%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4217	42.17%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.7708	77.08%
skin sensitisation	-	0.8712	87.12%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9303	93.03%
Acute Oral Toxicity (c)	III	0.7198	71.98%
Estrogen receptor binding	+	0.6698	66.98%
Androgen receptor binding	-	0.5229	52.29%
Thyroid receptor binding	-	0.5832	58.32%
Glucocorticoid receptor binding	+	0.6950	69.50%
Aromatase binding	+	0.5620	56.20%
PPAR gamma	+	0.5691	56.91%
Honey bee toxicity	-	0.8169	81.69%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9186	91.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.33%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.89%	95.89%
CHEMBL261	P00915	Carbonic anhydrase I	94.86%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.47%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.94%	96.77%
CHEMBL2581	P07339	Cathepsin D	93.61%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.37%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.85%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.75%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.35%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.93%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.26%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.09%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.68%	95.56%
CHEMBL4208	P20618	Proteasome component C5	89.53%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.07%	86.33%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.96%	90.95%
CHEMBL5555	O00767	Acyl-CoA desaturase	86.22%	97.50%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.08%	95.78%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.84%	82.67%
CHEMBL4040	P28482	MAP kinase ERK2	84.78%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.75%	99.17%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.93%	85.83%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.81%	82.38%

Plants that contains it

• Sarcocapnos baetica
• Sarcocapnos crassifolia

Cross-Links

• PubChem: 15690614
• LOTUS: LTS0169957
• wikiData: Q104396795