Stephanine

Details

• Internal ID: 6e6005b0-3546-41bd-b9d1-862a88d4cc08
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12R)-15-methoxy-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)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C2[C@H]1CC5=C4C=CC=C5OC)OCO3
• InChI: InChI=1S/C19H19NO3/c1-20-7-6-11-8-16-19(23-10-22-16)18-12-4-3-5-15(21-2)13(12)9-14(20)17(11)18/h3-5,8,14H,6-7,9-10H2,1-2H3/t14-/m1/s1
• InChI Key: UEAPAHNNFSZHMW-CQSZACIVSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₃
• Molecular Weight: 309.40 g/mol
• Exact Mass: 309.13649347 g/mol
• Topological Polar Surface Area (TPSA): 30.90 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 517-63-5
• CHEMBL601020
• (12R)-15-methoxy-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
• DTXSID90965972
• BDBM50306887
• AKOS040762374
• (-)-Stephanine; (R)-(-)-Stephanine; 8-Methoxy-1,2-(methylenedioxy)-6a-aporphine; Stephanin; l-Stephanine
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-9-methoxy-7-methyl-, (R)-
• 9-Methoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9699	96.99%
Caco-2	+	0.9601	96.01%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.5786	57.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9383	93.83%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7444	74.44%
P-glycoprotein inhibitior	-	0.8148	81.48%
P-glycoprotein substrate	-	0.5464	54.64%
CYP3A4 substrate	+	0.6465	64.65%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	-	0.6163	61.63%
CYP2C9 inhibition	-	0.9398	93.98%
CYP2C19 inhibition	-	0.7280	72.80%
CYP2D6 inhibition	+	0.9165	91.65%
CYP1A2 inhibition	+	0.7908	79.08%
CYP2C8 inhibition	-	0.7392	73.92%
CYP inhibitory promiscuity	+	0.5072	50.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6345	63.45%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9822	98.22%
Skin irritation	-	0.7922	79.22%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	+	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8180	81.80%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8553	85.53%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6314	63.14%
Acute Oral Toxicity (c)	III	0.6062	60.62%
Estrogen receptor binding	+	0.5406	54.06%
Androgen receptor binding	+	0.5739	57.39%
Thyroid receptor binding	-	0.4936	49.36%
Glucocorticoid receptor binding	+	0.8449	84.49%
Aromatase binding	-	0.7405	74.05%
PPAR gamma	+	0.7191	71.91%
Honey bee toxicity	-	0.7914	79.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9024	90.24%

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	98.89%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.45%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.07%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.86%	86.33%
CHEMBL2056	P21728	Dopamine D1 receptor	93.54%	91.00%
CHEMBL2535	P11166	Glucose transporter	92.65%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.43%	93.40%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	91.45%	96.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.41%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.77%	91.11%
CHEMBL240	Q12809	HERG	88.10%	89.76%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	87.18%	94.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.16%	92.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.98%	95.78%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	86.25%	100.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.12%	82.67%
CHEMBL5747	Q92793	CREB-binding protein	85.96%	95.12%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.92%	96.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.76%	99.18%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.60%	89.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.43%	90.95%
CHEMBL217	P14416	Dopamine D2 receptor	85.39%	95.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.35%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.16%	93.99%
CHEMBL261	P00915	Carbonic anhydrase I	83.08%	96.76%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.03%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.79%	89.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.75%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.44%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.24%	94.00%
CHEMBL5406	Q86X55	Histone-arginine methyltransferase CARM1	82.11%	94.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.74%	82.38%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.32%	92.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.92%	100.00%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	80.75%	89.32%

Plants that contains it

• Fibraurea recisa
• Magnolia coco
• Stephania abyssinica
• Stephania bancroftii
• Stephania cephalantha
• Stephania delavayi
• Stephania japonica
• Stephania venosa
• Xylopia aethiopica

Cross-Links

• PubChem: 160501
• NPASS: NPC225774
• LOTUS: LTS0182610
• wikiData: Q72508879