Capaurine

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	432609dc-82d2-41dd-90c0-edb2af954c7f
Taxonomy	Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name	(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-1-ol
SMILES (Canonical)	COC1=C(C2=C(CC3C4=C(C(=C(C=C4CCN3C2)OC)OC)O)C=C1)OC
SMILES (Isomeric)	COC1=C(C2=C(C[C@H]3C4=C(C(=C(C=C4CCN3C2)OC)OC)O)C=C1)OC
InChI	InChI=1S/C21H25NO5/c1-24-16-6-5-12-9-15-18-13(10-17(25-2)21(27-4)19(18)23)7-8-22(15)11-14(12)20(16)26-3/h5-6,10,15,23H,7-9,11H2,1-4H3/t15-/m0/s1
InChI Key	GSPIMPLJQOCBFY-HNNXBMFYSA-N
Popularity	14 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₅NO₅
Molecular Weight	371.40 g/mol
Exact Mass	371.17327290 g/mol
Topological Polar Surface Area (TPSA)	60.40 Å²
XlogP	2.90
Atomic LogP (AlogP)	3.08
H-Bond Acceptor	6
H-Bond Donor	1
Rotatable Bonds	4

Synonyms

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(-)-Capaurine

l-Capaurine

478-14-8

NSC 404532

2,3,9,10-Tetramethoxy-13a-alpha-berbin-1-ol

CHEBI:3366

(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-1-ol

13aalpha-Berbin-1-ol, 2,3,9,10-tetramethoxy-

13a-alpha-Berbin-1-ol, 2,3,9,10-tetramethoxy-

(S)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-1-ol

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	+	0.7969	79.69%
Caco-2	+	0.8749	87.49%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7219	72.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9329	93.29%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.4700	47.00%
P-glycoprotein inhibitior	-	0.5214	52.14%
P-glycoprotein substrate	-	0.5217	52.17%
CYP3A4 substrate	+	0.6125	61.25%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8566	85.66%
CYP2C9 inhibition	-	0.9439	94.39%
CYP2C19 inhibition	-	0.7236	72.36%
CYP2D6 inhibition	-	0.5068	50.68%
CYP1A2 inhibition	+	0.6094	60.94%
CYP2C8 inhibition	+	0.4826	48.26%
CYP inhibitory promiscuity	-	0.9014	90.14%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6377	63.77%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9618	96.18%
Skin irritation	-	0.7688	76.88%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8015	80.15%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8914	89.14%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9047	90.47%
Acute Oral Toxicity (c)	III	0.4507	45.07%
Estrogen receptor binding	+	0.6595	65.95%
Androgen receptor binding	+	0.5341	53.41%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	-	0.4907	49.07%
Aromatase binding	-	0.6971	69.71%
PPAR gamma	-	0.6039	60.39%
Honey bee toxicity	-	0.8755	87.55%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5951	59.51%
Fish aquatic toxicity	-	0.4511	45.11%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL217	P14416	Dopamine D2 receptor	98.23%	95.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.65%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.64%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.89%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.76%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.60%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.21%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	89.56%	95.12%
CHEMBL2056	P21728	Dopamine D1 receptor	89.09%	91.00%
CHEMBL2535	P11166	Glucose transporter	88.84%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.71%	94.45%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	87.53%	91.79%
CHEMBL3438	Q05513	Protein kinase C zeta	86.84%	88.48%
CHEMBL4208	P20618	Proteasome component C5	86.05%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.82%	82.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.80%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.63%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.87%	93.99%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.61%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.55%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.33%	99.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.06%	91.03%
CHEMBL2581	P07339	Cathepsin D	81.90%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.64%	85.14%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.07%	100.00%
CHEMBL5905	Q04828	Aldo-keto reductase family 1 member C1	80.23%	91.79%

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.

Stephania lincangensis

Stephania pierrei

Uvaria dulcis