Stylopin

Details

• Internal ID: c685e4ed-6c50-4611-a6e9-73882a23d871
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene
• SMILES (Canonical): C1CN2CC3=C(CC2C4=CC5=C(C=C41)OCO5)C=CC6=C3OCO6
• SMILES (Isomeric): C1CN2CC3=C(C[C@@H]2C4=CC5=C(C=C41)OCO5)C=CC6=C3OCO6
• InChI: InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m1/s1
• InChI Key: UXYJCYXWJGAKQY-OAHLLOKOSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.30 g/mol
• Exact Mass: 323.11575802 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (S)-Stylopin
• Stylopin
• UNII-J0JS75Q12Z
• (-)-Tetrahydrocoptisine
• l-Stylopine
• J0JS75Q12Z
• 84-39-9
• (+-)-Stylopine
• Coptisine, tetrahydro-
• (1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene
• (+-)-Tetrahydrocoptisine
• 2,3:9,10-Bis(methylenedioxy)-13a-alpha-berbine
• C19H17NO4
• 13a-alpha-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-
• NSC-110382
• (R)-stylopine
• Stylopine (VAN)
• (+)-Stylopine
• STYLOPINE [MI]
• 2,3:9,10-BIS(METHYLENEDIOXY)-(-)-TETRAHYDROBERBERINE
• SCHEMBL14703887
• 4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-, (S)-
• 4H-BIS(1,3)BENZODIOXOLO(5,6-A:4',5'-G)QUINOLIZINE, 6,7,12B,13-TETRAHYDRO-, (12BS)-
• AKOS000277993
• AKOS016023688
• NSC 404529
• Berbine, 2,3:9,10-bis(methylenedioxy)-, (+-)-
• Q27280991
• 13A.ALPHA.-BERBINE, 2,3:9,10-BIS(METHYLENEDIOXY)-
• 4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-
• 4H-Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine, 6,7,12b,13-tetrahydro-, (+-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	+	0.8516	85.16%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5937	59.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9420	94.20%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8710	87.10%
P-glycoprotein inhibitior	-	0.5684	56.84%
P-glycoprotein substrate	-	0.7798	77.98%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5820	58.20%
CYP2D6 substrate	+	0.6456	64.56%
CYP3A4 inhibition	+	0.5325	53.25%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.5469	54.69%
CYP2D6 inhibition	+	0.8397	83.97%
CYP1A2 inhibition	+	0.9345	93.45%
CYP2C8 inhibition	-	0.8446	84.46%
CYP inhibitory promiscuity	+	0.6570	65.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5621	56.21%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.7149	71.49%
Skin corrosion	-	0.9298	92.98%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8819	88.19%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8490	84.90%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6125	61.25%
Acute Oral Toxicity (c)	III	0.6766	67.66%
Estrogen receptor binding	+	0.6918	69.18%
Androgen receptor binding	+	0.6149	61.49%
Thyroid receptor binding	-	0.5192	51.92%
Glucocorticoid receptor binding	+	0.5555	55.55%
Aromatase binding	-	0.5366	53.66%
PPAR gamma	+	0.6771	67.71%
Honey bee toxicity	-	0.7934	79.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7834	78.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.50%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.40%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	92.56%	95.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.01%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.02%	96.77%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	88.09%	83.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.05%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.83%	98.95%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.32%	90.95%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.19%	82.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.38%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.90%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.75%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.72%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.88%	90.24%
CHEMBL261	P00915	Carbonic anhydrase I	82.77%	96.76%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	82.05%	96.42%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.03%	80.96%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.81%	89.62%

Plants that contains it

• Chelidonium majus
• Corydalis nobilis
• Corydalis pallida
• Corydalis saxicola
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Fibraurea recisa
• Fumaria vaillantii
• Hylomecon japonica
• Strychnos nux-vomica

Cross-Links

• PubChem: 697545
• NPASS: NPC268214
• LOTUS: LTS0034202
• wikiData: Q27280991