Narcotine hemiacetal

Details

• Internal ID: 1455637c-65ae-4bc7-9270-3bfe9891da85
• Taxonomy: Organoheterocyclic compounds > Tetrahydroisoquinolines
• IUPAC Name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol
• InChI: InChI=1S/C22H25NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18,22,24H,7-8,10H2,1-4H3/t17-,18+,22?/m1/s1
• InChI Key: TZNFGVJRQISOHK-HVHHGIHYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅NO₇
• Molecular Weight: 415.40 g/mol
• Exact Mass: 415.16310214 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• noscapine hemiacetal
• (-)-narcotine hemiacetal
• (-)-noscapine hemiacetal
• (-)-alpha-narcotine hemiacetal
• SCHEMBL29363061
• CHEBI:141667
• C20297
• (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8557	85.57%
Caco-2	+	0.8572	85.72%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4469	44.69%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.9422	94.22%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9000	90.00%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	-	0.7670	76.70%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6661	66.61%
CYP3A4 inhibition	+	0.5711	57.11%
CYP2C9 inhibition	+	0.7577	75.77%
CYP2C19 inhibition	+	0.7912	79.12%
CYP2D6 inhibition	-	0.7388	73.88%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	-	0.6592	65.92%
CYP inhibitory promiscuity	-	0.6163	61.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5498	54.98%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9641	96.41%
Skin irritation	-	0.7928	79.28%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4805	48.05%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8727	87.27%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8831	88.31%
Acute Oral Toxicity (c)	III	0.7677	76.77%
Estrogen receptor binding	+	0.8123	81.23%
Androgen receptor binding	-	0.5540	55.40%
Thyroid receptor binding	+	0.5913	59.13%
Glucocorticoid receptor binding	+	0.8207	82.07%
Aromatase binding	-	0.5215	52.15%
PPAR gamma	+	0.7333	73.33%
Honey bee toxicity	-	0.8761	87.61%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.6790	67.90%

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	99.27%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.85%	93.99%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.53%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.50%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.09%	95.56%
CHEMBL261	P00915	Carbonic anhydrase I	92.16%	96.76%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	91.11%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.69%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.59%	92.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.13%	82.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.08%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.58%	86.33%
CHEMBL205	P00918	Carbonic anhydrase II	88.57%	98.44%
CHEMBL2056	P21728	Dopamine D1 receptor	86.96%	91.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.85%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.43%	94.00%
CHEMBL2535	P11166	Glucose transporter	85.68%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.20%	91.11%
CHEMBL4208	P20618	Proteasome component C5	83.60%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.44%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.04%	95.78%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.83%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.45%	89.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.21%	97.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.83%	85.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.61%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.18%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.02%	89.50%

Plants that contains it

• Papaver orientale

Cross-Links

• PubChem: 90657121
• LOTUS: LTS0148904
• wikiData: Q74417739