Emetine

Details

• Internal ID: a8ef8a3c-d9f3-414b-add6-2ab5a78493d4
• Taxonomy: Alkaloids and derivatives > Emetine alkaloids
• IUPAC Name: (2S,3R,11bS)-2-[[(1R)-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
• 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/t18-,21-,24+,25-/m0/s1
• InChI Key: AUVVAXYIELKVAI-CKBKHPSWSA-N
• Popularity: 4,347 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

• 483-18-1
• Emetin
• Cephaeline methyl ether
• Methyl cephaeline
• 6',7',10,11-Tetramethoxyemetan
• (-)-Emetine
• Cephaline-O-methyl ether
• Emetinum
• Emetan, 6',7',10,11-tetramethoxy-
• X8D5EPO80M
• NSC-33669
• CHEBI:4781
• DTXSID5022980
• (2S,3R,11bS)-2-[[(1R)-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
• DTXCID402980
• Ipecine
• Methylcephaeline
• (2S,3R,11bS)-2-(((1R)-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
• RefChem:136683
• 207-592-1
• Emetine (>90%)
• TCMDC-125531
• CHEMBL50588
• GNF-PF-196
• Emetine dihydrochloride hydrate
• Emetine [BAN]
• (2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-2H-benzo[a]quinolizine
• CAS-483-18-1
• 6',7',10,11-tetrakis(methyloxy)emetan
• HSDB 2150
• EINECS 207-592-1
• UNII-X8D5EPO80M
• BRN 0100829
• SR-01000000081
• SR-01000075853
• NCGC00024379-04
• 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)-
• YAT
• 6',7',10,11-Tetramethoxy-emetan
• EMETINE [VANDF]
• EMETINUM [HPUS]
• EMETINE [HSDB]
• EMETINE [MI]
• Prestwick3_000570
• EMETINE [WHO-DD]
• CBiol_002059
• Lopac0_000460
• SCHEMBL56277
• BSPBio_000360
• BPBio1_000396
• SCHEMBL29390500
• BDBM38871
• cid_6603320
• GTPL11087
• Bio1_000345
• Bio1_000834
• Bio1_001323
• GLXC-15435
• HY-B1479
• Tox21_110901
• BDBM50216297
• MFCD00242944
• STL565152
• 6'',7'',10,11-tetramethoxyemetan
• AKOS037623356
• Tox21_110901_1
• CCG-204552
• DB13393
• FE22663
• SDCCGSBI-0050445.P002
• NCGC00024379-05
• NCGC00024379-06
• NCGC00024379-07
• NCGC00024379-08
• NCGC00024379-09
• NCGC00024379-10
• NCGC00024379-11
• NCGC00024379-12
• NCGC00024379-13
• NCGC00024379-14
• NCGC00024379-16
• NCGC00024379-17
• NCGC00024379-24
• NCGC00024379-25
• NCGC00024379-29
• DA-63172
• NCI60_002959
• CS-0013180
• NS00005212
• C09421
• Q3050386
• SR-01000000081-3
• SR-01000000081-5
• SR-01000075853-5
• BRD-K03067624-001-01-5
• BRD-K03067624-001-02-3
• BRD-K03067624-300-02-9
• 6',7',10,11-Tetramethoxy-emetan;Emetine;(-)-Emetine
• Emetine hydrochloride, European Pharmacopoeia (EP) Reference Standard
• Emetine hydrochloride, United States Pharmacopeia (USP) Reference Standard
• 2H-BENZO(A)QUINOLIZINE, 3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-2-(((1R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-, (2S,3R,11BS)-
• 2H-Benzo[a]quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-(2S,3R,11bS)-

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
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	38 nM	IC50	via CMAUP
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	182 nM	IC50	via CMAUP
CHEMBL2535	P11166	Glucose transporter	108 nM	IC50	DOI: 10.6019/CHEMBL3433997
CHEMBL5514	P42858	Huntingtin	354.8 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	398.1 nM	Potency	via Super-PRED
CHEMBL4302	P08183	P-glycoprotein 1	130300 nM; 115600 nM; 2400 nM; 35100 nM; 9200 nM; 9600 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 11716514
CHEMBL1293235	P02545	Prelamin-A/C	177.8 nM; 794.3 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1075121	O75884	Putative hydrolase RBBP9	7800 nM	IC50	PMID: 20207142
CHEMBL1293294	P51151	Ras-related protein Rab-9A	18356.4 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	5211.9 nM; 1849.3 nM	Potency; Potency	via CMAUP; via CMAUP
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
• Carapichea klugii
• Hedera helix

Cross-Links

• PubChem: 10219
• NPASS: NPC187022
• ChEMBL: CHEMBL50588
• LOTUS: LTS0024375
• wikiData: Q3050386