(3,17,18-Trimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15,17,19-hexaen-19-yl)methanol

Details

• Internal ID: 5d04ee39-842d-4c7a-867b-e9acc9d131b3
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (3,17,18-trimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15,17,19-hexaen-19-yl)methanol
• SMILES (Canonical): COC1=C(C(=C2CC3C4=C(C5=C(C=C4CCN3CC2=C1)OCO5)OC)CO)OC
• SMILES (Isomeric): COC1=C(C(=C2CC3C4=C(C5=C(C=C4CCN3CC2=C1)OCO5)OC)CO)OC
• InChI: InChI=1S/C22H25NO6/c1-25-17-7-13-9-23-5-4-12-6-18-21(29-11-28-18)22(27-3)19(12)16(23)8-14(13)15(10-24)20(17)26-2/h6-7,16,24H,4-5,8-11H2,1-3H3
• InChI Key: RJZGHQFMKACAHM-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅NO₆
• Molecular Weight: 399.40 g/mol
• Exact Mass: 399.16818752 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• SR-01000082432-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6756	67.56%
Caco-2	+	0.8017	80.17%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5199	51.99%
OATP2B1 inhibitior	-	0.8668	86.68%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.9262	92.62%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8780	87.80%
P-glycoprotein inhibitior	-	0.5349	53.49%
P-glycoprotein substrate	-	0.5857	58.57%
CYP3A4 substrate	+	0.6117	61.17%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	+	0.6526	65.26%
CYP3A4 inhibition	+	0.6437	64.37%
CYP2C9 inhibition	-	0.8719	87.19%
CYP2C19 inhibition	-	0.5295	52.95%
CYP2D6 inhibition	-	0.5800	58.00%
CYP1A2 inhibition	+	0.5121	51.21%
CYP2C8 inhibition	-	0.5587	55.87%
CYP inhibitory promiscuity	+	0.5815	58.15%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5741	57.41%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9597	95.97%
Skin irritation	-	0.7905	79.05%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	+	0.6046	60.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3863	38.63%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8662	86.62%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8100	81.00%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.6780	67.80%
Androgen receptor binding	-	0.5141	51.41%
Thyroid receptor binding	+	0.5758	57.58%
Glucocorticoid receptor binding	+	0.7563	75.63%
Aromatase binding	-	0.6487	64.87%
PPAR gamma	+	0.5476	54.76%
Honey bee toxicity	-	0.8155	81.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	-	0.3991	39.91%

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	98.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.20%	91.11%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	91.61%	96.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.94%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.79%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.65%	94.45%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.55%	82.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL261	P00915	Carbonic anhydrase I	87.32%	96.76%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.97%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.62%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.29%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.76%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.71%	82.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.64%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.42%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.25%	94.00%
CHEMBL4208	P20618	Proteasome component C5	84.89%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.79%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	84.52%	95.12%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.94%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.40%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.47%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.21%	95.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.51%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.33%	100.00%

Plants that contains it

• Meconopsis punicea
• Papaver bracteatum
• Papaver cambricum
• Papaver canescens
• Papaver lateritium
• Papaver lisae
• Papaver orientale
• Papaver pygmaeum
• Platycladus orientalis

Cross-Links

• PubChem: 633984
• NPASS: NPC83120
• LOTUS: LTS0102928
• wikiData: Q105238230