Narcotoline

Details

• Internal ID: 0cab64d6-b014-49b3-b3b9-6eff43df74d3
• Taxonomy: Alkaloids and derivatives > Phthalide isoquinolines
• IUPAC Name: (3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one
• SMILES (Canonical): CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3
• InChI: InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1
• InChI Key: LMGZCSKYOKDBES-AEFFLSMTSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁NO₇
• Molecular Weight: 399.40 g/mol
• Exact Mass: 399.13180201 g/mol
• Topological Polar Surface Area (TPSA): 86.70 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 521-40-4
• desmethylnarcotine
• EINECS 208-313-6
• UNII-M5V1K1QE3F
• M5V1K1QE3F
• (3S)-3-[(5R)-4-hydroxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one
• C09593
• NARCOTOLINE [MI]
• (-)-NARCOTOLINE
• SCHEMBL309428
• CHEBI:7482
• C21H21NO7
• DTXSID50200098
• (S-(R*,R*))-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)phthalide
• [S-(R*,R*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)phthalide
• Q6965699
• (3S)-6,7-DIMETHOXY-3-((5R)-5,6,7,8-TETRAHYDRO-4-HYDROXY-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)-1(3H)-ISOBENZOFURANONE
• 1(3H)-ISOBENZOFURANONE, 6,7-DIMETHOXY-3-((5R)-5,6,7,8-TETRAHYDRO-4-HYDROXY-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)-, (3S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7662	76.62%
Caco-2	+	0.8191	81.91%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4883	48.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9213	92.13%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8253	82.53%
P-glycoprotein inhibitior	+	0.8378	83.78%
P-glycoprotein substrate	-	0.8543	85.43%
CYP3A4 substrate	+	0.6822	68.22%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.6702	67.02%
CYP3A4 inhibition	+	0.5587	55.87%
CYP2C9 inhibition	+	0.7527	75.27%
CYP2C19 inhibition	+	0.7076	70.76%
CYP2D6 inhibition	-	0.8509	85.09%
CYP1A2 inhibition	-	0.9319	93.19%
CYP2C8 inhibition	-	0.6404	64.04%
CYP inhibitory promiscuity	-	0.6464	64.64%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5590	55.90%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.7947	79.47%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6293	62.93%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8762	87.62%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8622	86.22%
Acute Oral Toxicity (c)	III	0.7215	72.15%
Estrogen receptor binding	+	0.7683	76.83%
Androgen receptor binding	-	0.7886	78.86%
Thyroid receptor binding	-	0.6667	66.67%
Glucocorticoid receptor binding	+	0.7929	79.29%
Aromatase binding	-	0.6166	61.66%
PPAR gamma	+	0.8096	80.96%
Honey bee toxicity	-	0.8352	83.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.7772	77.72%

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	98.03%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.46%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.31%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.06%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.06%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.52%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.06%	93.99%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.21%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.05%	95.89%
CHEMBL2056	P21728	Dopamine D1 receptor	90.22%	91.00%
CHEMBL2535	P11166	Glucose transporter	89.76%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.41%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.11%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.41%	82.67%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	88.38%	82.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.06%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.82%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.15%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	84.71%	95.62%
CHEMBL4208	P20618	Proteasome component C5	83.78%	90.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.06%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.70%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.17%	95.78%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.35%	97.33%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.29%	96.86%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.00%	89.62%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Papaver somniferum

Cross-Links

• PubChem: 442330
• NPASS: NPC92707
• LOTUS: LTS0233952
• wikiData: Q6965699