methyl (E)-2-[(2S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Details

• Internal ID: e9e9321d-1919-473f-b89c-eae442928671
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: methyl (E)-2-[(2S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• SMILES (Canonical): CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=CC=C4)OC
• SMILES (Isomeric): CCC1CN2CCC3=C([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=CC=C4)OC
• InChI: InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14?,16-,19-/m0/s1
• InChI Key: LELBFTMXCIIKKX-STILVGNPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.50 g/mol
• Exact Mass: 398.22055744 g/mol
• Topological Polar Surface Area (TPSA): 63.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Corynan-16-carboxylic acid, 16,17-didehydro-9,17-dimethoxy-, methyl ester, (16E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9832	98.32%
Caco-2	+	0.8068	80.68%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6585	65.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9202	92.02%
OATP1B3 inhibitior	+	0.8564	85.64%
MATE1 inhibitior	-	0.8037	80.37%
OCT2 inhibitior	-	0.6389	63.89%
BSEP inhibitior	+	0.9713	97.13%
P-glycoprotein inhibitior	+	0.8549	85.49%
P-glycoprotein substrate	+	0.7885	78.85%
CYP3A4 substrate	+	0.6674	66.74%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	+	0.3485	34.85%
CYP3A4 inhibition	-	0.7337	73.37%
CYP2C9 inhibition	-	0.7679	76.79%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	+	0.5137	51.37%
CYP1A2 inhibition	+	0.5908	59.08%
CYP2C8 inhibition	+	0.5737	57.37%
CYP inhibitory promiscuity	+	0.6524	65.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6208	62.08%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9802	98.02%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9204	92.04%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5740	57.40%
Acute Oral Toxicity (c)	III	0.7386	73.86%
Estrogen receptor binding	+	0.7020	70.20%
Androgen receptor binding	+	0.7837	78.37%
Thyroid receptor binding	+	0.5392	53.92%
Glucocorticoid receptor binding	+	0.7983	79.83%
Aromatase binding	-	0.7195	71.95%
PPAR gamma	-	0.5656	56.56%
Honey bee toxicity	-	0.8357	83.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9806	98.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL237	P41145	Kappa opioid receptor	198 nM; 116 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	39.2 nM; 161 nM	EC50; Ki	via Super-PRED; 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	99.62%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.89%	94.45%
CHEMBL2535	P11166	Glucose transporter	95.81%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.46%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.58%	97.25%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.82%	91.79%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.56%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.21%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.51%	86.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.38%	97.50%
CHEMBL5028	O14672	ADAM10	83.35%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.71%	94.33%
CHEMBL255	P29275	Adenosine A2b receptor	82.27%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.62%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.59%	99.23%

Plants that contains it

• Mitragyna speciosa

Cross-Links

• PubChem: 57856495
• NPASS: NPC34408
• LOTUS: LTS0083391
• wikiData: Q104399096