(6aS)-9-Hydroxy-1,2,10-trimethoxy-4,5,6,6aalpha-tetrahydro-7H-dibenzo[de,g]quinoline-6-carboxylic acid methyl ester

Details

• Internal ID: d06a4b63-9c3f-43c5-8219-cdb8632100bb
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: methyl (6aS)-9-hydroxy-1,2,10-trimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-carboxylate
• SMILES (Canonical): COC1=C(C2=C3C(CC4=CC(=C(C=C42)OC)O)N(CCC3=C1)C(=O)OC)OC
• SMILES (Isomeric): COC1=C(C2=C3[C@H](CC4=CC(=C(C=C42)OC)O)N(CCC3=C1)C(=O)OC)OC
• InChI: InChI=1S/C21H23NO6/c1-25-16-10-13-12(8-15(16)23)7-14-18-11(5-6-22(14)21(24)28-4)9-17(26-2)20(27-3)19(13)18/h8-10,14,23H,5-7H2,1-4H3/t14-/m0/s1
• InChI Key: CMJDWJRGWFWFKE-AWEZNQCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.40 g/mol
• Exact Mass: 385.15253745 g/mol
• Topological Polar Surface Area (TPSA): 77.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6963	69.63%
Caco-2	+	0.8728	87.28%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7255	72.55%
OATP2B1 inhibitior	-	0.8657	86.57%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9388	93.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.8006	80.06%
P-glycoprotein inhibitior	-	0.6349	63.49%
P-glycoprotein substrate	-	0.6313	63.13%
CYP3A4 substrate	+	0.6267	62.67%
CYP2C9 substrate	-	0.8224	82.24%
CYP2D6 substrate	+	0.5283	52.83%
CYP3A4 inhibition	-	0.8627	86.27%
CYP2C9 inhibition	-	0.9275	92.75%
CYP2C19 inhibition	-	0.6862	68.62%
CYP2D6 inhibition	-	0.7445	74.45%
CYP1A2 inhibition	+	0.5554	55.54%
CYP2C8 inhibition	-	0.5645	56.45%
CYP inhibitory promiscuity	-	0.7074	70.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6695	66.95%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9343	93.43%
Skin irritation	-	0.7934	79.34%
Skin corrosion	-	0.9529	95.29%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7447	74.47%
skin sensitisation	-	0.9110	91.10%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7918	79.18%
Acute Oral Toxicity (c)	III	0.5712	57.12%
Estrogen receptor binding	+	0.8018	80.18%
Androgen receptor binding	-	0.4833	48.33%
Thyroid receptor binding	+	0.6445	64.45%
Glucocorticoid receptor binding	+	0.8930	89.30%
Aromatase binding	-	0.6161	61.61%
PPAR gamma	+	0.6356	63.56%
Honey bee toxicity	-	0.8811	88.11%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.9500	95.00%

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	99.24%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	97.31%	95.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.64%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.73%	95.56%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.55%	91.79%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.25%	93.03%
CHEMBL2535	P11166	Glucose transporter	91.10%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.62%	99.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.29%	93.40%
CHEMBL2056	P21728	Dopamine D1 receptor	89.04%	91.00%
CHEMBL261	P00915	Carbonic anhydrase I	88.56%	96.76%
CHEMBL340	P08684	Cytochrome P450 3A4	88.20%	91.19%
CHEMBL4208	P20618	Proteasome component C5	88.17%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.65%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.33%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.51%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.22%	90.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.19%	91.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.60%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.09%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.11%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.82%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.76%	94.45%
CHEMBL3438	Q05513	Protein kinase C zeta	80.15%	88.48%
CHEMBL5028	O14672	ADAM10	80.12%	97.50%

Plants that contains it

• Bursera simaruba
• Cephalaria leucantha
• Cissus quadrangularis
• Cleome trachysperma
• Delphinium denudatum
• Diplacus aurantiacus
• Ericameria laricifolia
• Litsea cubeba
• Loranthus longiflorus
• Melaleuca glauca
• Mentha longifolia subsp. longifolia
• Ormosia fordiana
• Orthosiphon wulfenioides
• Podocarpus elatus
• Polygala senega
• Solanum scabrum
• Stevia rebaudiana
• Vachellia karroo

Cross-Links

• PubChem: 44206920
• NPASS: NPC310907
• LOTUS: LTS0073111
• wikiData: Q104964629