Emetamine

Details

• Internal ID: e47b3cf3-a4ae-47c7-943b-d58afac85988
• Taxonomy: Organoheterocyclic compounds > Quinolizidines
• IUPAC Name: (2R,3R,11bS)-2-[(6,7-dimethoxyisoquinolin-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=C3C2CC1CC4=NC=CC5=CC(=C(C=C54)OC)OC)OC)OC
• SMILES (Isomeric): CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1CC4=NC=CC5=CC(=C(C=C54)OC)OC)OC)OC
• InChI: InChI=1S/C29H36N2O4/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/h7,9,13-16,18,21,25H,6,8,10-12,17H2,1-5H3/t18-,21-,25-/m0/s1
• InChI Key: MBYXEBXZARTUSS-HMHJJOSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆N₂O₄
• Molecular Weight: 476.60 g/mol
• Exact Mass: 476.26750763 g/mol
• Topological Polar Surface Area (TPSA): 53.10 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.46
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 483-19-2
• UNII-CWM13I408S
• CWM13I408S
• (2R,3R,11bS)-2-[(6,7-dimethoxyisoquinolin-1-yl)methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
• 6',7',10,11-tetramethoxy-1',2',3',4'-tetradehydroemetan
• EMETAMINE [MI]
• TETRADEHYDROEMETINE
• C09420
• CHEBI:4780
• SCHEMBL3219787
• DTXSID30197477
• Q27106477
• 1',2',3',4'-TETRADEHYDRO-6',7',10,11-TETRAMETHOXYEMETAN
• EMETAN, 1',2',3',4'-TETRADEHYDRO-6',7',10,11-TETRAMETHOXY-
• 2H-BENZO(A)QUINOLIZINE, 2-((6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-, (2R,3R,11BS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	+	0.6077	60.77%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6014	60.14%
OATP2B1 inhibitior	-	0.5762	57.62%
OATP1B1 inhibitior	+	0.9298	92.98%
OATP1B3 inhibitior	+	0.9361	93.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.9948	99.48%
P-glycoprotein inhibitior	+	0.8262	82.62%
P-glycoprotein substrate	+	0.9284	92.84%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.7273	72.73%
CYP3A4 inhibition	-	0.7266	72.66%
CYP2C9 inhibition	-	0.9435	94.35%
CYP2C19 inhibition	-	0.9413	94.13%
CYP2D6 inhibition	-	0.7404	74.04%
CYP1A2 inhibition	-	0.8915	89.15%
CYP2C8 inhibition	+	0.6506	65.06%
CYP inhibitory promiscuity	-	0.5585	55.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6660	66.60%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9667	96.67%
Skin irritation	-	0.7875	78.75%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9810	98.10%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5053	50.53%
skin sensitisation	-	0.8961	89.61%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7194	71.94%
Acute Oral Toxicity (c)	III	0.7055	70.55%
Estrogen receptor binding	+	0.8595	85.95%
Androgen receptor binding	+	0.7336	73.36%
Thyroid receptor binding	+	0.7622	76.22%
Glucocorticoid receptor binding	+	0.8214	82.14%
Aromatase binding	+	0.6175	61.75%
PPAR gamma	+	0.5364	53.64%
Honey bee toxicity	-	0.8245	82.45%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.7224	72.24%

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	98.62%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	97.72%	92.94%
CHEMBL5747	Q92793	CREB-binding protein	97.71%	95.12%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.05%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	96.12%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.24%	86.33%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	91.40%	92.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.49%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.81%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.38%	93.99%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	87.37%	98.33%
CHEMBL202	P00374	Dihydrofolate reductase	87.20%	89.92%
CHEMBL2581	P07339	Cathepsin D	87.10%	98.95%
CHEMBL2535	P11166	Glucose transporter	87.10%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.87%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.61%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.43%	99.17%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	85.44%	95.71%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.37%	93.10%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	84.87%	90.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.95%	82.38%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.90%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.59%	95.89%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	83.16%	96.69%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	82.89%	96.47%
CHEMBL5014	O43353	Serine/threonine-protein kinase RIPK2	82.24%	86.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.55%	97.09%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.53%	94.03%
CHEMBL4158	P49327	Fatty acid synthase	81.44%	82.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.31%	95.89%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	81.12%	96.25%
CHEMBL2319	P06870	Kallikrein 1	80.69%	90.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.49%	91.11%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 442217
• NPASS: NPC294731