(+/-)-Nantenine

Details

• Internal ID: 2c7afa73-fe58-4831-b02f-f4e79969fabd
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 18,19-dimethoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC4=CC5=C(C=C43)OCO5)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2C1CC4=CC5=C(C=C43)OCO5)OC)OC
• InChI: InChI=1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3
• InChI Key: WSVWKHTVFGTTKJ-UHFFFAOYSA-N
• Popularity: 11 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

• 42971-15-3
• Thalictruberine
• CHEMBL467094
• SCHEMBL1254591
• DTXSID00962816
• BDBM50114920
• 1,2-dimethoxy-9,10-methylenedioxyaporphine
• 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H,10H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
• 4H-Benzo(de)(1,3)benzodioxolo(5,6-g)quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9459	94.59%
Caco-2	+	0.9301	93.01%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.5163	51.63%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.9388	93.88%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7101	71.01%
P-glycoprotein inhibitior	-	0.6681	66.81%
P-glycoprotein substrate	-	0.8239	82.39%
CYP3A4 substrate	+	0.6211	62.11%
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	-	0.7774	77.74%
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	-	0.9827	98.27%
Skin irritation	-	0.8002	80.02%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8283	82.83%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.7449	74.49%
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	-	0.7278	72.78%
Acute Oral Toxicity (c)	III	0.7399	73.99%
Estrogen receptor binding	+	0.6017	60.17%
Androgen receptor binding	-	0.5821	58.21%
Thyroid receptor binding	+	0.6046	60.46%
Glucocorticoid receptor binding	+	0.7962	79.62%
Aromatase binding	-	0.5112	51.12%
PPAR gamma	+	0.7106	71.06%
Honey bee toxicity	-	0.8223	82.23%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9362	93.62%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	2 nM; 430 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	340 nM	Ki	via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	252 nM	Ki	via Super-PRED
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	181 nM	Ki	via Super-PRED
CHEMBL2056	P21728	Dopamine D1 receptor	895 nM	Ki	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	858 nM	Ki	via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	309 nM	Ki	via Super-PRED
CHEMBL219	P21917	Dopamine D4 receptor	262 nM	Ki	via Super-PRED
CHEMBL1941	P25021	Histamine H2 receptor	672 nM	Ki	via Super-PRED
CHEMBL1898	P28222	Serotonin 1b (5-HT1b) receptor	100 nM	Ki	via Super-PRED
CHEMBL1983	P28221	Serotonin 1d (5-HT1d) receptor	49 nM	Ki	via Super-PRED
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	832 nM	Ki	via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	543 nM	Ki	via Super-PRED
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	257 nM	Ki	via Super-PRED
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	67 nM	Ki	via Super-PRED
CHEMBL228	P31645	Serotonin transporter	244 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.02%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.22%	96.09%
CHEMBL5747	Q92793	CREB-binding protein	93.75%	95.12%
CHEMBL261	P00915	Carbonic anhydrase I	92.84%	96.76%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	92.43%	96.86%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.42%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.34%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	90.16%	82.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.98%	82.67%
CHEMBL3438	Q05513	Protein kinase C zeta	89.08%	88.48%
CHEMBL2581	P07339	Cathepsin D	88.66%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.60%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.03%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.73%	95.78%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.36%	89.62%
CHEMBL4208	P20618	Proteasome component C5	85.63%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.30%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.29%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.01%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.99%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.40%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.08%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.00%	99.17%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.86%	89.50%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.52%	92.38%
CHEMBL2535	P11166	Glucose transporter	81.50%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.48%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.45%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.22%	95.89%

Plants that contains it

• Cassytha pubescens
• Dehaasia incrassata
• Nandina domestica
• Ocotea macrophylla

Cross-Links

• PubChem: 181743
• LOTUS: LTS0119545
• wikiData: Q82944584