(7aS)-6,7,7aalpha,8-Tetrahydro-7-methyl-9,10-dimethoxy-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline

Details

• Internal ID: b9e3fe25-6b89-419d-a32e-8bf78ae99862
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12S)-15,16-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaene
• SMILES (Canonical): CN1CCC2=CC3=C(C4=C2C1CC5=C4C=CC(=C5OC)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=C4C=CC(=C5OC)OC)OCO3
• InChI: InChI=1S/C20H21NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8,14H,6-7,9-10H2,1-3H3/t14-/m0/s1
• InChI Key: UVDQDNQWGQFIAO-AWEZNQCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.40 g/mol
• Exact Mass: 339.14705815 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• C20H21NO4
• CHEMBL387840
• BDBM50197847
• (7aS)-6,7,7aalpha,8-Tetrahydro-7-methyl-9,10-dimethoxy-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9200	92.00%
Caco-2	+	0.9539	95.39%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.5417	54.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9327	93.27%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.5665	56.65%
P-glycoprotein inhibitior	-	0.6258	62.58%
P-glycoprotein substrate	-	0.6172	61.72%
CYP3A4 substrate	+	0.6457	64.57%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	+	0.6954	69.54%
CYP2C9 inhibition	-	0.8752	87.52%
CYP2C19 inhibition	+	0.6349	63.49%
CYP2D6 inhibition	+	0.7681	76.81%
CYP1A2 inhibition	-	0.6842	68.42%
CYP2C8 inhibition	-	0.7066	70.66%
CYP inhibitory promiscuity	-	0.5481	54.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9801	98.01%
Skin irritation	-	0.8038	80.38%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	+	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7751	77.51%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7953	79.53%
Acute Oral Toxicity (c)	III	0.7109	71.09%
Estrogen receptor binding	+	0.5900	59.00%
Androgen receptor binding	-	0.5061	50.61%
Thyroid receptor binding	+	0.5629	56.29%
Glucocorticoid receptor binding	+	0.8289	82.89%
Aromatase binding	-	0.6325	63.25%
PPAR gamma	+	0.7344	73.44%
Honey bee toxicity	-	0.8208	82.08%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9413	94.13%

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%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.06%	96.77%
CHEMBL240	Q12809	HERG	96.75%	89.76%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.03%	93.40%
CHEMBL5747	Q92793	CREB-binding protein	94.85%	95.12%
CHEMBL2056	P21728	Dopamine D1 receptor	94.31%	91.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.02%	91.49%
CHEMBL261	P00915	Carbonic anhydrase I	92.86%	96.76%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.27%	82.67%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	91.88%	96.86%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.87%	95.78%
CHEMBL217	P14416	Dopamine D2 receptor	89.73%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.38%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.34%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.02%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.25%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.11%	89.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.06%	82.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.90%	91.11%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	86.82%	95.53%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.55%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.94%	89.50%
CHEMBL2535	P11166	Glucose transporter	85.82%	98.75%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.56%	90.95%
CHEMBL4040	P28482	MAP kinase ERK2	84.71%	83.82%
CHEMBL3438	Q05513	Protein kinase C zeta	84.67%	88.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.71%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.59%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.41%	93.99%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.27%	97.31%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.94%	85.83%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.54%	97.14%

Plants that contains it

• Ardisia crispa
• Doronicum grandiflorum
• Fissistigma oldhamii
• Leibnitzia anandria
• Lithocarpus haipinii
• Oxytropis lanata
• Populus balsamifera
• Sphaerophysa salsula
• Stephania abyssinica
• Stephania bancroftii
• Stephania cephalantha
• Stephania venosa
• Strychnos gossweileri
• Xylopia aethiopica

Cross-Links

• PubChem: 10042806
• NPASS: NPC313133
• LOTUS: LTS0180640
• wikiData: Q105279773