O-Methylpsychotrine

Details

• Internal ID: d9fd2e98-bb40-484c-bf40-f0acc7c2d492
• Taxonomy: Alkaloids and derivatives > Emetine alkaloids
• IUPAC Name: (2R,3R,11bS)-2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-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=NCCC5=CC(=C(C=C54)OC)OC)OC)OC
• SMILES (Isomeric): CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1CC4=NCCC5=CC(=C(C=C54)OC)OC)OC)OC
• InChI: InChI=1S/C29H38N2O4/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/h13-16,18,21,25H,6-12,17H2,1-5H3/t18-,21-,25-/m0/s1
• InChI Key: FBRKYRSUSJWLHH-HMHJJOSWSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈N₂O₄
• Molecular Weight: 478.60 g/mol
• Exact Mass: 478.28315770 g/mol
• Topological Polar Surface Area (TPSA): 52.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.10
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• Methylpsychotrine
• Methylpsychotrin
• 1',2'-Dehydroemetin
• 523-01-3
• CHEBI:81067
• Emetan, 1',2'-didehydro-6',7',10,11-tetramethoxy-
• EINECS 208-339-8
• UNII-V7C64CD3BR
• V7C64CD3BR
• CHEMBL471812
• 2H-Benzo[a]quinolizine, 2-[(3,4-dihydro-6,7-dimethoxy-1-isoquinolinyl)methyl]-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-, (2R,3R,11bS)-
• 2H-BENZO(A)QUINOLIZINE, 2-((3,4-DIHYDRO-6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-3-ETHYL-1,3,4,6,7,11B-HEXAHYDRO-9,10-DIMETHOXY-, (2R,3R,11BS)-
• Psychotrine, O-methyl-
• SCHEMBL181482
• 1',2'-DEHYDROEMETINE
• O-METHYLPSYCHOTRINE [MI]
• DTXSID70200318
• BDBM50478516
• Psychotrine, O-methyl- (6CI,7CI)
• (2R,3R,11bS)-2-[(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
• LS-63848
• C17411
• Q27155023

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9403	94.03%
Caco-2	+	0.5764	57.64%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6089	60.89%
OATP2B1 inhibitior	-	0.5771	57.71%
OATP1B1 inhibitior	+	0.9184	91.84%
OATP1B3 inhibitior	+	0.9360	93.60%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.9854	98.54%
P-glycoprotein inhibitior	+	0.6364	63.64%
P-glycoprotein substrate	+	0.8439	84.39%
CYP3A4 substrate	+	0.6629	66.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5118	51.18%
CYP3A4 inhibition	-	0.6796	67.96%
CYP2C9 inhibition	-	0.9401	94.01%
CYP2C19 inhibition	-	0.9338	93.38%
CYP2D6 inhibition	-	0.6579	65.79%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	-	0.6347	63.47%
CYP inhibitory promiscuity	-	0.8694	86.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6729	67.29%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9549	95.49%
Skin irritation	-	0.7776	77.76%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9671	96.71%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8828	88.28%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4563	45.63%
Acute Oral Toxicity (c)	III	0.6877	68.77%
Estrogen receptor binding	+	0.8774	87.74%
Androgen receptor binding	+	0.7131	71.31%
Thyroid receptor binding	+	0.7766	77.66%
Glucocorticoid receptor binding	+	0.8375	83.75%
Aromatase binding	+	0.5992	59.92%
PPAR gamma	+	0.6013	60.13%
Honey bee toxicity	-	0.7767	77.67%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.8231	82.31%

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	99.26%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	96.67%	92.94%
CHEMBL5747	Q92793	CREB-binding protein	94.68%	95.12%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.69%	95.89%
CHEMBL2581	P07339	Cathepsin D	93.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.12%	86.33%
CHEMBL261	P00915	Carbonic anhydrase I	90.01%	96.76%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.43%	95.89%
CHEMBL284	P27487	Dipeptidyl peptidase IV	88.41%	95.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.57%	95.17%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.40%	82.38%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.93%	93.40%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	86.61%	96.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.78%	85.14%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	85.53%	98.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.39%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.29%	97.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.22%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.53%	97.09%
CHEMBL2094108	P49354	Protein farnesyltransferase	83.35%	97.92%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	82.95%	96.86%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.78%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.71%	99.17%
CHEMBL5203	P33316	dUTP pyrophosphatase	82.26%	99.18%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.22%	92.38%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.76%	96.67%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.13%	89.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.10%	91.03%

Plants that contains it

• Carapichea ipecacuanha

Cross-Links

• PubChem: 65033
• NPASS: NPC216816
• ChEMBL: CHEMBL471812