10,24-Dimethoxy-6,8,20,22-tetraoxa-14-azahexacyclo[12.11.0.03,12.04,9.017,25.019,23]pentacosa-3,9,11,17,19(23),24-hexaene

Details

• Internal ID: e6714145-15b6-426e-8b56-cf8b89c6874e
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 10,24-dimethoxy-6,8,20,22-tetraoxa-14-azahexacyclo[12.11.0.03,12.04,9.017,25.019,23]pentacosa-3,9,11,17,19(23),24-hexaene
• SMILES (Canonical): COC1=C2C(=C3CC4C5=C(C6=C(C=C5CCN4CC3=C1)OCO6)OC)COCO2
• SMILES (Isomeric): COC1=C2C(=C3CC4C5=C(C6=C(C=C5CCN4CC3=C1)OCO6)OC)COCO2
• InChI: InChI=1S/C22H23NO6/c1-24-17-6-13-8-23-4-3-12-5-18-21(29-11-27-18)22(25-2)19(12)16(23)7-14(13)15-9-26-10-28-20(15)17/h5-6,16H,3-4,7-11H2,1-2H3
• InChI Key: QJZHAQOTBKWPGS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃NO₆
• Molecular Weight: 397.40 g/mol
• Exact Mass: 397.15253745 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9640	96.40%
Caco-2	+	0.8286	82.86%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4616	46.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9400	94.00%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8492	84.92%
P-glycoprotein inhibitior	-	0.4483	44.83%
P-glycoprotein substrate	-	0.6204	62.04%
CYP3A4 substrate	+	0.6237	62.37%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	+	0.5369	53.69%
CYP2C9 inhibition	-	0.8906	89.06%
CYP2C19 inhibition	+	0.6591	65.91%
CYP2D6 inhibition	+	0.8677	86.77%
CYP1A2 inhibition	+	0.9075	90.75%
CYP2C8 inhibition	-	0.5646	56.46%
CYP inhibitory promiscuity	+	0.7364	73.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5729	57.29%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9542	95.42%
Skin irritation	-	0.7949	79.49%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7512	75.12%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8437	84.37%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4513	45.13%
Acute Oral Toxicity (c)	III	0.6032	60.32%
Estrogen receptor binding	+	0.5748	57.48%
Androgen receptor binding	+	0.5523	55.23%
Thyroid receptor binding	+	0.5551	55.51%
Glucocorticoid receptor binding	+	0.7589	75.89%
Aromatase binding	-	0.6323	63.23%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7569	75.69%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.6632	66.32%

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	97.80%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	97.09%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.70%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.86%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.26%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	91.09%	95.12%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	90.57%	82.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.18%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.04%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.65%	82.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.25%	92.62%
CHEMBL2581	P07339	Cathepsin D	86.04%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.99%	95.56%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	85.48%	96.25%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.40%	96.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.37%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	84.02%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.40%	85.14%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.23%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.78%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.36%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.15%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.87%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.34%	97.09%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.40%	90.95%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.27%	90.24%

Plants that contains it

• Papaver bracteatum

Cross-Links

• PubChem: 595827
• LOTUS: LTS0011641
• wikiData: Q105222983