3-Methoxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1,3,8,10,12,14(22),15,17(21)-octaen-12-ol

Details

• Internal ID: 38843c59-d0dd-4af3-bb80-fc8049f89040
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
• IUPAC Name: 3-methoxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1,3,8,10,12,14(22),15,17(21)-octaen-12-ol
• SMILES (Canonical): COC1=C2C(=CC3=CC(=C4C5=C(CNC4=C31)C6=C(C=C5)OCO6)O)OCO2
• SMILES (Isomeric): COC1=C2C(=CC3=CC(=C4C5=C(CNC4=C31)C6=C(C=C5)OCO6)O)OCO2
• InChI: InChI=1S/C20H15NO6/c1-23-20-15-9(5-14-19(20)27-8-25-14)4-12(22)16-10-2-3-13-18(26-7-24-13)11(10)6-21-17(15)16/h2-5,21-22H,6-8H2,1H3
• InChI Key: YRNZUSFZAMIXBD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₅NO₆
• Molecular Weight: 365.30 g/mol
• Exact Mass: 365.08993720 g/mol
• Topological Polar Surface Area (TPSA): 78.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.60
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9097	90.97%
Caco-2	+	0.7681	76.81%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.3779	37.79%
OATP2B1 inhibitior	-	0.8679	86.79%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7949	79.49%
P-glycoprotein inhibitior	+	0.6273	62.73%
P-glycoprotein substrate	-	0.6814	68.14%
CYP3A4 substrate	+	0.5452	54.52%
CYP2C9 substrate	-	0.8141	81.41%
CYP2D6 substrate	+	0.4620	46.20%
CYP3A4 inhibition	+	0.5528	55.28%
CYP2C9 inhibition	-	0.5965	59.65%
CYP2C19 inhibition	+	0.5837	58.37%
CYP2D6 inhibition	+	0.6377	63.77%
CYP1A2 inhibition	+	0.5211	52.11%
CYP2C8 inhibition	+	0.6069	60.69%
CYP inhibitory promiscuity	+	0.7559	75.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5531	55.31%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.6984	69.84%
Skin irritation	-	0.7941	79.41%
Skin corrosion	-	0.9412	94.12%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3793	37.93%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8201	82.01%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6034	60.34%
Acute Oral Toxicity (c)	III	0.6683	66.83%
Estrogen receptor binding	+	0.9369	93.69%
Androgen receptor binding	+	0.5927	59.27%
Thyroid receptor binding	+	0.7341	73.41%
Glucocorticoid receptor binding	+	0.8449	84.49%
Aromatase binding	+	0.5532	55.32%
PPAR gamma	+	0.8306	83.06%
Honey bee toxicity	-	0.8701	87.01%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.6068	60.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.46%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.96%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.89%	94.45%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	93.99%	93.24%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.18%	82.67%
CHEMBL4208	P20618	Proteasome component C5	91.72%	90.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	91.37%	81.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.73%	93.99%
CHEMBL2581	P07339	Cathepsin D	90.34%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.54%	94.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.29%	80.96%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.77%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.13%	99.15%
CHEMBL2535	P11166	Glucose transporter	87.69%	98.75%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	87.11%	91.79%
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	86.86%	94.70%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.56%	92.88%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.49%	85.30%
CHEMBL1951	P21397	Monoamine oxidase A	85.24%	91.49%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.09%	93.10%
CHEMBL240	Q12809	HERG	84.91%	89.76%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.77%	96.67%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.32%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.46%	92.62%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.11%	96.39%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.56%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.08%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	81.10%	95.12%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	81.00%	92.68%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.72%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.40%	93.40%

Plants that contains it

• Chelidonium majus

Cross-Links

• PubChem: 101601460
• NPASS: NPC127143
• LOTUS: LTS0192267
• wikiData: Q104394027