(S)-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	2861a591-46a9-441c-883b-3c2558c23f4f
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	(13aS)-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(C[C@H]3C4=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/t15-/m0/s1
InChI Key	KNWVMRVOBAFFMH-HNNXBMFYSA-N
Popularity	210 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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Scoulerine

Scoulerin

6451-73-6

(-)-Scoulerine

Aequaline

(-)-Scoulerin

(13aS)-3,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-2,9-diol

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

MLS002153900

CHEBI:17129

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
CHEMBL1795093	O14727	Apoptotic protease-activating factor 1	16300 nM	IC50	via CMAUP
CHEMBL2056	P21728	Dopamine D1 receptor	22 nM 22 nM 529 nM	Ki Ki Ki	PMID: 23332346 via Super-PRED via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	214 nM 214 nM	Ki Ki	PMID: 23332346 via Super-PRED
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	15848.9 nM	Potency	via CMAUP

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.