Boldine 2-methyl ether

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	6995590f-3af0-43a5-b945-d6c040e14ef4
Taxonomy	Alkaloids and derivatives > Aporphines
IUPAC Name	(6aS)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-ol
SMILES (Canonical)	CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)OC
SMILES (Isomeric)	CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)OC
InChI	InChI=1S/C20H23NO4/c1-21-6-5-11-9-17(24-3)20(25-4)19-13-10-16(23-2)15(22)8-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1
InChI Key	ZFLRVRLYWHNAEC-AWEZNQCLSA-N
Popularity	9 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₀H₂₃NO₄
Molecular Weight	341.40 g/mol
Exact Mass	341.16270821 g/mol
Topological Polar Surface Area (TPSA)	51.20 Å²
XlogP	3.00
Atomic LogP (AlogP)	3.17
H-Bond Acceptor	5
H-Bond Donor	1
Rotatable Bonds	3

Synonyms

Top

N-Methyllaurotetanine

2169-44-0

Rogersine

Boldine 2-methyl ether

NSC 247564

2-O-METHYLBOLDINE

(+)-N-Methyllaurotetanine

11558LRZ50

NSC 247506

NSC-247506

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8819	88.19%
Caco-2	+	0.9035	90.35%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5850	58.50%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.6038	60.38%
P-glycoprotein inhibitior	-	0.8474	84.74%
P-glycoprotein substrate	-	0.7625	76.25%
CYP3A4 substrate	+	0.6135	61.35%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9083	90.83%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8238	82.38%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7089	70.89%
CYP inhibitory promiscuity	-	0.9392	93.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7108	71.08%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7431	74.31%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7125	71.25%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.7949	79.49%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9012	90.12%
Acute Oral Toxicity (c)	III	0.7730	77.30%
Estrogen receptor binding	+	0.5964	59.64%
Androgen receptor binding	-	0.6027	60.27%
Thyroid receptor binding	+	0.6256	62.56%
Glucocorticoid receptor binding	+	0.7717	77.17%
Aromatase binding	-	0.5251	52.51%
PPAR gamma	+	0.6654	66.54%
Honey bee toxicity	-	0.8891	88.91%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.8882	88.82%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2056	P21728	Dopamine D1 receptor	373 nM 373 nM	Ki Ki	PMID: 25695425 via Super-PRED
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	314 nM 85 nM 85 nM	Ki Ki Ki	PMID: 25695425 PMID: 16562853 via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	323 nM 323 nM	Ki Ki	PMID: 25695425 via Super-PRED
CHEMBL3426	P47898	Serotonin 5a (5-HT5a) receptor	566 nM 566 nM	Ki Ki	PMID: 25695425 via Super-PRED
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	306 nM 306 nM	Ki Ki	via Super-PRED PMID: 25695425
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	20 nM 20 nM	Ki Ki	via Super-PRED PMID: 25695425

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.15%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	98.09%	95.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.11%	91.79%
CHEMBL3438	Q05513	Protein kinase C zeta	91.70%	88.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	90.78%	95.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.45%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.43%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.24%	91.03%
CHEMBL4208	P20618	Proteasome component C5	89.63%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.61%	98.95%
CHEMBL2535	P11166	Glucose transporter	87.11%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.57%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.28%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.19%	89.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.15%	82.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.85%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.56%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	85.53%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.50%	94.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.32%	96.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.31%	99.17%
CHEMBL261	P00915	Carbonic anhydrase I	84.15%	96.76%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.12%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.16%	93.99%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Aconitum paniculigerum var. wulingense

Actinodaphne speciosa

Alseodaphne perakensis

Alstonia angustiloba

Amphiachyris dracunculoides

Baccharis grandicapitulata

Beesia calthifolia

Boschniakia rossica