(6S,6aR)-2,3,9,10-tetramethoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-1-ol

Details

• Internal ID: f2823762-ae5f-4527-92e3-3eb7e7fdb893
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (6S,6aR)-2,3,9,10-tetramethoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-1-ol
• SMILES (Canonical): C[N+]1(CCC2=C3C1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)O)OC)OC)[O-]
• SMILES (Isomeric): C[N@@+]1(CCC2=C3[C@H]1CC4=CC(=C(C=C4C3=C(C(=C2OC)OC)O)OC)OC)[O-]
• InChI: InChI=1S/C21H25NO6/c1-22(24)7-6-12-17-14(22)8-11-9-15(25-2)16(26-3)10-13(11)18(17)19(23)21(28-5)20(12)27-4/h9-10,14,23H,6-8H2,1-5H3/t14-,22+/m1/s1
• InChI Key: OSXSNRJLKQQRJZ-PEBXRYMYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₆
• Molecular Weight: 387.40 g/mol
• Exact Mass: 387.16818752 g/mol
• Topological Polar Surface Area (TPSA): 75.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7863	78.63%
Caco-2	+	0.8190	81.90%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3260	32.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.4941	49.41%
P-glycoprotein inhibitior	-	0.6447	64.47%
P-glycoprotein substrate	-	0.6889	68.89%
CYP3A4 substrate	+	0.6026	60.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6854	68.54%
CYP3A4 inhibition	-	0.7269	72.69%
CYP2C9 inhibition	-	0.8909	89.09%
CYP2C19 inhibition	-	0.8150	81.50%
CYP2D6 inhibition	-	0.7211	72.11%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.7105	71.05%
CYP inhibitory promiscuity	-	0.9796	97.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5989	59.89%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8688	86.88%
Skin irritation	-	0.7737	77.37%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4790	47.90%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8555	85.55%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9100	91.00%
Acute Oral Toxicity (c)	III	0.6513	65.13%
Estrogen receptor binding	+	0.8150	81.50%
Androgen receptor binding	+	0.5259	52.59%
Thyroid receptor binding	+	0.7617	76.17%
Glucocorticoid receptor binding	+	0.8120	81.20%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.7438	74.38%
Honey bee toxicity	-	0.8646	86.46%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5451	54.51%
Fish aquatic toxicity	+	0.8399	83.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL241	Q14432	Phosphodiesterase 3A	97.24%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.00%	96.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.40%	91.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.04%	91.11%
CHEMBL2056	P21728	Dopamine D1 receptor	90.63%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.52%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.29%	99.17%
CHEMBL217	P14416	Dopamine D2 receptor	89.26%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.26%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.97%	93.40%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	88.92%	98.21%
CHEMBL2535	P11166	Glucose transporter	88.75%	98.75%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	88.13%	95.70%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.95%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.06%	94.00%
CHEMBL3438	Q05513	Protein kinase C zeta	84.67%	88.48%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.98%	92.68%
CHEMBL4208	P20618	Proteasome component C5	82.74%	90.00%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	82.19%	89.32%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.07%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.73%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	81.09%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.15%	92.38%

Plants that contains it

• Thalictrum simplex

Cross-Links

• PubChem: 163193512
• LOTUS: LTS0039742
• wikiData: Q105199380