5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-ol, 6,7,7a,8-tetrahydro-9,10-dimethoxy-7-methyl-, (7aS,8R)-

Details

• Internal ID: b4bec3c1-fc7c-4c0d-862a-d42f333a78f5
• Taxonomy: Alkaloids and derivatives > Aporphines > Hydroxy-7-aporphines
• IUPAC Name: (12S,13R)-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-hexaen-13-ol
• SMILES (Canonical): CN1CCC2=CC3=C(C4=C2C1C(C5=C4C=CC(=C5OC)OC)O)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C2[C@H]1[C@@H](C5=C4C=CC(=C5OC)OC)O)OCO3
• InChI: InChI=1S/C20H21NO5/c1-21-7-6-10-8-13-20(26-9-25-13)15-11-4-5-12(23-2)19(24-3)16(11)18(22)17(21)14(10)15/h4-5,8,17-18,22H,6-7,9H2,1-3H3/t17-,18+/m0/s1
• InChI Key: RUNAFDLOXRYAAQ-ZWKOTPCHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.14197277 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-ol, 6,7,7a,8-tetrahydro-9,10-dimethoxy-7-methyl-, (7aS,8R)-
• DTXSID101002668
• 9,10-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinolin-8-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6966	69.66%
Caco-2	+	0.9224	92.24%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4786	47.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6786	67.86%
P-glycoprotein inhibitior	-	0.5679	56.79%
P-glycoprotein substrate	-	0.6270	62.70%
CYP3A4 substrate	+	0.6266	62.66%
CYP2C9 substrate	-	0.6063	60.63%
CYP2D6 substrate	+	0.6929	69.29%
CYP3A4 inhibition	-	0.7443	74.43%
CYP2C9 inhibition	-	0.5284	52.84%
CYP2C19 inhibition	+	0.5354	53.54%
CYP2D6 inhibition	-	0.6957	69.57%
CYP1A2 inhibition	-	0.8573	85.73%
CYP2C8 inhibition	-	0.7086	70.86%
CYP inhibitory promiscuity	-	0.6724	67.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5690	56.90%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9751	97.51%
Skin irritation	-	0.7873	78.73%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6466	64.66%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8676	86.76%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8617	86.17%
Acute Oral Toxicity (c)	III	0.7150	71.50%
Estrogen receptor binding	+	0.6558	65.58%
Androgen receptor binding	-	0.5806	58.06%
Thyroid receptor binding	+	0.5754	57.54%
Glucocorticoid receptor binding	+	0.7689	76.89%
Aromatase binding	+	0.5257	52.57%
PPAR gamma	+	0.7760	77.60%
Honey bee toxicity	-	0.8255	82.55%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6573	65.73%

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	98.90%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.47%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.89%	96.77%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.73%	82.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.25%	93.40%
CHEMBL4208	P20618	Proteasome component C5	92.20%	90.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	91.72%	97.31%
CHEMBL261	P00915	Carbonic anhydrase I	91.34%	96.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.90%	95.78%
CHEMBL1951	P21397	Monoamine oxidase A	90.57%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.24%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.83%	86.33%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	89.78%	96.86%
CHEMBL2056	P21728	Dopamine D1 receptor	89.55%	91.00%
CHEMBL2581	P07339	Cathepsin D	88.60%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.02%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.95%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.50%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.46%	91.11%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.21%	89.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.99%	89.62%
CHEMBL5747	Q92793	CREB-binding protein	84.92%	95.12%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	84.31%	85.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.85%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.83%	82.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.32%	100.00%
CHEMBL2535	P11166	Glucose transporter	81.12%	98.75%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.85%	90.95%

Plants that contains it

• Cardiopetalum calophyllum
• Stephania venosa

Cross-Links

• PubChem: 158088
• LOTUS: LTS0095504
• wikiData: Q82996901