(+/-)-Dicentrine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	91cf1a98-f72f-4b91-93cb-d36f2aa66676
Taxonomy	Alkaloids and derivatives > Aporphines
IUPAC Name	16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
SMILES (Canonical)	CN1CCC2=CC3=C(C4=C2C1CC5=CC(=C(C=C54)OC)OC)OCO3
SMILES (Isomeric)	CN1CCC2=CC3=C(C4=C2C1CC5=CC(=C(C=C54)OC)OC)OCO3
InChI	InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3
InChI Key	YJWBWQWUHVXPNC-UHFFFAOYSA-N
Popularity	37 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₀H₂₁NO₄
Molecular Weight	339.40 g/mol
Exact Mass	339.14705815 g/mol
Topological Polar Surface Area (TPSA)	40.20 Å²
XlogP	3.20
Atomic LogP (AlogP)	3.18
H-Bond Acceptor	5
H-Bond Donor	0
Rotatable Bonds	2

Synonyms

Top

Dicentrine, (+/-)-

Dicentrine DL-form [MI]

26110-43-0

UNII-J3IJ5DN3JE

J3IJ5DN3JE

L-DICENTRINE

28832-07-7

10,11-DIMETHOXY-7-METHYL-6,7,7A,8-TETRAHYDRO-5H-[1,3]DIOXOLO[4',5':4,5]BENZO[1,2,3-DE]BENZO[G]QUINOLINE

5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-

CN1CCc2cc3OCOc3c4c5cc(OC)c(OC)cc5CC1c24

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

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9459	94.59%
Caco-2	+	0.9386	93.86%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.5163	51.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9281	92.81%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7254	72.54%
P-glycoprotein inhibitior	-	0.6307	63.07%
P-glycoprotein substrate	-	0.7194	71.94%
CYP3A4 substrate	+	0.6112	61.12%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	+	0.6228	62.28%
CYP2C9 inhibition	-	0.8237	82.37%
CYP2C19 inhibition	+	0.7057	70.57%
CYP2D6 inhibition	+	0.7688	76.88%
CYP1A2 inhibition	-	0.7119	71.19%
CYP2C8 inhibition	-	0.8520	85.20%
CYP inhibitory promiscuity	-	0.5422	54.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5880	58.80%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9652	96.52%
Skin irritation	-	0.8002	80.02%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	+	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7799	77.99%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.7949	79.49%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6923	69.23%
Acute Oral Toxicity (c)	III	0.7399	73.99%
Estrogen receptor binding	+	0.6823	68.23%
Androgen receptor binding	-	0.6037	60.37%
Thyroid receptor binding	+	0.5850	58.50%
Glucocorticoid receptor binding	+	0.8325	83.25%
Aromatase binding	-	0.5181	51.81%
PPAR gamma	+	0.7505	75.05%
Honey bee toxicity	-	0.7798	77.98%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9362	93.62%

Targets

Top

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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.59%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.39%	96.77%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	92.93%	96.86%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	92.45%	82.67%
CHEMBL5747	Q92793	CREB-binding protein	92.03%	95.12%
CHEMBL2581	P07339	Cathepsin D	91.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.73%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.67%	93.40%
CHEMBL2056	P21728	Dopamine D1 receptor	90.45%	91.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.65%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.62%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.89%	95.89%
CHEMBL261	P00915	Carbonic anhydrase I	86.94%	96.76%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.57%	95.78%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	86.53%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.34%	82.38%
CHEMBL3438	Q05513	Protein kinase C zeta	85.92%	88.48%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.85%	92.94%
CHEMBL4208	P20618	Proteasome component C5	85.85%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.97%	89.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.92%	89.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.40%	93.99%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.24%	92.38%
CHEMBL217	P14416	Dopamine D2 receptor	84.16%	95.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.80%	94.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.67%	91.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.05%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.21%	97.14%
CHEMBL6031	Q9H9B1	Histone-lysine N-methyltransferase, H3 lysine-9 specific 5	80.89%	94.33%
CHEMBL2535	P11166	Glucose transporter	80.62%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.54%	91.11%

Plants that contains it

Top

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.

Albertisia delagoensis

Cassytha filiformis

Cissampelos capensis

Dasymaschalon sootepense