Scoulerine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	cd74ad92-3a7f-46ec-a6db-8b8d1d68ad09
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol
SMILES (Canonical)	COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
SMILES (Isomeric)	COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
InChI	InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3
InChI Key	KNWVMRVOBAFFMH-UHFFFAOYSA-N
Popularity	30 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₉H₂₁NO₄
Molecular Weight	327.40 g/mol
Exact Mass	327.14705815 g/mol
Topological Polar Surface Area (TPSA)	62.20 Å²
XlogP	2.60
Atomic LogP (AlogP)	2.77
H-Bond Acceptor	5
H-Bond Donor	2
Rotatable Bonds	2

Synonyms

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Discretamine

l-Scoulerine

605-34-5

(R,S)-Scoulerine

l-Skoulerine

6451-72-5

CHEBI:31033

2,9-Dioxy-3,10-dimethoxyberbine

3,10-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-2,9-diol

13a-alpha-BERBINE-2,9-DIOL, 3,10-DIMETHOXY-

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8639	86.39%
Caco-2	+	0.8469	84.69%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7978	79.78%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.9424	94.24%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5503	55.03%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5873	58.73%
CYP3A4 substrate	+	0.5990	59.90%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8690	86.90%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8332	83.32%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.5967	59.67%
CYP inhibitory promiscuity	-	0.8633	86.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6645	66.45%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9297	92.97%
Skin irritation	-	0.7164	71.64%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4624	46.24%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8933	89.33%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6794	67.94%
Acute Oral Toxicity (c)	III	0.4740	47.40%
Estrogen receptor binding	+	0.6245	62.45%
Androgen receptor binding	+	0.5288	52.88%
Thyroid receptor binding	+	0.6306	63.06%
Glucocorticoid receptor binding	+	0.6648	66.48%
Aromatase binding	-	0.6914	69.14%
PPAR gamma	+	0.5500	55.00%
Honey bee toxicity	-	0.8974	89.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6251	62.51%
Fish aquatic toxicity	-	0.3947	39.47%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2056	P21728	Dopamine D1 receptor	22 nM 529 nM	Ki Ki	via Super-PRED via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	214 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.52%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.18%	91.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.53%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.63%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.57%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.18%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.10%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.99%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	90.27%	88.48%
CHEMBL2581	P07339	Cathepsin D	89.28%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.71%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.43%	95.56%
CHEMBL2535	P11166	Glucose transporter	87.50%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.65%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.00%	90.71%
CHEMBL4208	P20618	Proteasome component C5	83.69%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.33%	82.38%
CHEMBL5747	Q92793	CREB-binding protein	83.28%	95.12%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.73%	91.03%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.15%	93.99%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.09%	100.00%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.96%	96.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.57%	99.17%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Annona leptopetala

Argemone ochroleuca

Bocconia frutescens

Capnoides sempervirens

Corydalis gortschakovii

Corydalis incisa

Corydalis nobilis