alpha-Narcotinediol

Details

• Internal ID: 0aec6a9c-74b2-4f84-b08c-cf0e50d42a6e
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: [2-(hydroxymethyl)-3,4-dimethoxyphenyl]-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol
• InChI: InChI=1S/C22H27NO7/c1-23-8-7-12-9-16-21(30-11-29-16)22(28-4)17(12)18(23)19(25)13-5-6-15(26-2)20(27-3)14(13)10-24/h5-6,9,18-19,24-25H,7-8,10-11H2,1-4H3
• InChI Key: BHLLOBXLOWXZDQ-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇NO₇
• Molecular Weight: 417.50 g/mol
• Exact Mass: 417.17875220 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 23942-99-6
• (-)-alpha-Narcotinediol
• MLS002920177
• [2-(hydroxymethyl)-3,4-dimethoxyphenyl]-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol
• alpha-Narcotinediol
• EINECS 245-946-7
• (-)-|A-Narcotinediol
• CHEMBL358914
• DTXSID30946765
• NSC132826
• NSC279531
• NSC 132826
• NSC 279531
• NSC-132826
• NSC-279531
• SMR001797774
• (S-(R*,S*))-3,4-Dimethoxy-alpha1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-o-xylene-alpha,alpha'-diol
• [2-(Hydroxymethyl)-3,4-dimethoxyphenyl](4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6424	64.24%
Caco-2	+	0.7981	79.81%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.4099	40.99%
OATP2B1 inhibitior	-	0.7306	73.06%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9384	93.84%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8876	88.76%
P-glycoprotein inhibitior	+	0.6759	67.59%
P-glycoprotein substrate	-	0.5762	57.62%
CYP3A4 substrate	+	0.6089	60.89%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	+	0.6299	62.99%
CYP3A4 inhibition	-	0.7834	78.34%
CYP2C9 inhibition	-	0.6930	69.30%
CYP2C19 inhibition	-	0.6471	64.71%
CYP2D6 inhibition	-	0.7700	77.00%
CYP1A2 inhibition	-	0.8707	87.07%
CYP2C8 inhibition	-	0.7094	70.94%
CYP inhibitory promiscuity	-	0.5770	57.70%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5654	56.54%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9775	97.75%
Skin irritation	-	0.7936	79.36%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4537	45.37%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8715	87.15%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.9776	97.76%
Acute Oral Toxicity (c)	III	0.6749	67.49%
Estrogen receptor binding	+	0.7211	72.11%
Androgen receptor binding	-	0.5985	59.85%
Thyroid receptor binding	+	0.5293	52.93%
Glucocorticoid receptor binding	+	0.7582	75.82%
Aromatase binding	+	0.5281	52.81%
PPAR gamma	+	0.5939	59.39%
Honey bee toxicity	-	0.8309	83.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4526	45.26%

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	99.34%	96.09%
CHEMBL261	P00915	Carbonic anhydrase I	96.30%	96.76%
CHEMBL2581	P07339	Cathepsin D	94.91%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.27%	93.99%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.42%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.39%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.82%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.82%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.77%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.34%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.91%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.86%	91.11%
CHEMBL4208	P20618	Proteasome component C5	88.20%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.90%	94.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	87.11%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.23%	89.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.07%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.15%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.95%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.52%	94.45%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.51%	100.00%
CHEMBL2535	P11166	Glucose transporter	83.41%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.44%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.98%	95.78%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.88%	82.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.82%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.31%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.29%	90.71%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.17%	90.95%

Plants that contains it

• Papaver orientale

Cross-Links

• PubChem: 98447
• LOTUS: LTS0021061
• wikiData: Q82924448