Isoemetine, tetradehydro-

Details

• Internal ID: 452770e2-dad1-44ad-8d67-9a8869bab301
• Taxonomy: Alkaloids and derivatives > Emetine alkaloids
• IUPAC Name: 2-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
• SMILES (Canonical): CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
• SMILES (Isomeric): CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
• InChI: InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3
• InChI Key: AUVVAXYIELKVAI-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀N₂O₄
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.29880776 g/mol
• Topological Polar Surface Area (TPSA): 52.20 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.94
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• NSC 33669
• GNF-Pf-5190
• Purum (Salt/Mix)
• Amebicide (Salt/Mix)
• CHEMBL192858
• MEGxp0_002048
• SCHEMBL13912579
• ACon0_000657
• DTXSID80859331
• AUVVAXYIELKVAI-UHFFFAOYSA-N
• 2H-Benzo(a)quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-((1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl)-
• NSC25464
• NSC-25464
• FT-0625656
• SW220072-1
• 1-({3-Ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH- pyrido[2,1-a]isoquinolin-2-yl}methyl)-6,7- dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 7005-82-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9601	96.01%
Caco-2	+	0.5412	54.12%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.6591	65.91%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9856	98.56%
P-glycoprotein inhibitior	-	0.8020	80.20%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6188	61.88%
CYP2C9 substrate	-	0.6339	63.39%
CYP2D6 substrate	+	0.8194	81.94%
CYP3A4 inhibition	-	0.8603	86.03%
CYP2C9 inhibition	-	0.9470	94.70%
CYP2C19 inhibition	-	0.9429	94.29%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9291	92.91%
CYP2C8 inhibition	-	0.6870	68.70%
CYP inhibitory promiscuity	-	0.9188	91.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7106	71.06%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9708	97.08%
Skin irritation	-	0.7407	74.07%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9836	98.36%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8930	89.30%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6179	61.79%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.8462	84.62%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.5781	57.81%
PPAR gamma	+	0.6073	60.73%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6703	67.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	354.8 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	398.1 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	177.8 nM; 794.3 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL5401	P42226	Signal transducer and activator of transcription 6	398.1 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	501.2 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	63.1 nM	Potency	via Super-PRED
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	501.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.96%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.83%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.80%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.57%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.32%	97.25%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.53%	97.21%
CHEMBL228	P31645	Serotonin transporter	92.04%	95.51%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.97%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.00%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.58%	98.95%
CHEMBL5747	Q92793	CREB-binding protein	87.77%	95.12%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.96%	89.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.63%	82.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.55%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.49%	90.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.99%	91.11%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.42%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.77%	95.89%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	81.57%	98.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.18%	89.50%
CHEMBL2535	P11166	Glucose transporter	80.13%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.10%	99.17%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.03%	92.38%

Plants that contains it

• Alangium longiflorum
• Carapichea ipecacuanha
• Hedera helix

Cross-Links

• PubChem: 9426
• LOTUS: LTS0070605
• wikiData: Q104919167