Dicentrine

Details

• Internal ID: b40ec68c-6f89-4289-9eb2-66a538498f1e
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12S)-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=C2[C@@H]1CC5=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/t14-/m0/s1
• InChI Key: YJWBWQWUHVXPNC-AWEZNQCLSA-N
• Popularity: 36 references in papers

Physical and Chemical Properties

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

Synonyms

• 517-66-8
• d-Dicentrine
• Dicentrin
• Eximine
• L-DICENTRINE
• O,N-Dimethyllitseferine
• (+)-dicentrine
• Dicentrine-(+)
• CCRIS 3806
• 28832-07-7
• 9,10-Dimethoxy-1,2-(methylenedioxy)aporphine
• UNII-J2ZGT5M0N7
• NSC 406035
• BRN 0095476
• J2ZGT5M0N7
• CHEMBL464748
• 1,2-Methylenedioxy-9,10-dimethoxyaporphine
• CHEBI:81079
• NSC406035
• NSC-406035
• 4-27-00-06486 (Beilstein Handbook Reference)
• 6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
• 9,10-Dimethoxy-1,2-(methylenedioxy)-6a.alpha.-aporphine
• 6a-alpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)- (9CI)
• 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
• CN1CCc2cc3OCOc3c4c5cc(OC)c(OC)cc5CC1c24
• DICENTRINE [MI]
• (R)-(-)-Dicentrine; L-Dicentrine; NSC 251699
• (S)-form;(+)-Dicentrine
• DICENTRINE, (+)-
• 9,2-(methylenedioxy)aporphine
• SCHEMBL6369440
• DICENTRINE D-FORM [MI]
• DTXSID10199651
• YJWBWQWUHVXPNC-AWEZNQCLSA-N
• (12S)-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
• HY-N6969
• BDBM50306885
• AKOS037514612
• LS-21473
• MS-25168
• CS-0026026
• C17426
• Q-100578
• Q15410930
• 6a.alpha.-Aporphine,10-dimethoxy-1,2-(methylenedioxy)-
• 5H-Benzo[g]-1,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
• (7aS)-6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
• 10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-, (S)-
• 5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE, 6,7,7A,8-TETRAHYDRO-10,11-DIMETHOXY-7-METHYL-, (7AS)-

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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

• Albertisia delagoensis
• Avena fatua
• Breynia vitis-idaea
• Cassytha filiformis
• Cissampelos capensis
• Cissampelos pareira
• Dicentra eximia
• Dicentra formosa
• Glaucium contortuplicatum
• Helichrysum fulvum
• Illigera luzonensis
• Lindera megaphylla
• Ocotea acutifolia
• Ocotea leucoxylon
• Ocotea macropoda
• Ocotea velloziana
• Piper sylvaticum
• Protea eximia
• Scolopia chinensis
• Sinomenium acutum
• Stephania abyssinica
• Stephania tetrandra
• Stephania zippeliana

Cross-Links

• PubChem: 101300
• NPASS: NPC16805
• ChEMBL: CHEMBL464748
• LOTUS: LTS0007524
• wikiData: Q15410930