methyl (2R)-2-[(2R,3Z,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate

Details

• Internal ID: 0af12374-db09-40ec-956e-fbad71616470
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: methyl (2R)-2-[(2R,3Z,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate
• SMILES (Canonical): CC=C1CN2CCC3=C(C2CC1C(CO)C(=O)OC)NC4=CC=CC=C34
• SMILES (Isomeric): C/C=C/1\CN2CCC3=C([C@@H]2C[C@@H]1[C@H](CO)C(=O)OC)NC4=CC=CC=C34
• InChI: InChI=1S/C21H26N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,16-17,19,22,24H,8-12H2,1-2H3/b13-3+/t16-,17-,19-/m0/s1
• InChI Key: RGXKJLTVROJBKZ-GUDANERBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.19434270 g/mol
• Topological Polar Surface Area (TPSA): 65.60 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• methyl (2R)-2-[(2R,3Z,12bS)-3-ethylidene-2,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-yl]-3-hydroxypropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9683	96.83%
Caco-2	+	0.8088	80.88%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7378	73.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8739	87.39%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	0.8496	84.96%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9317	93.17%
P-glycoprotein inhibitior	-	0.5128	51.28%
P-glycoprotein substrate	+	0.6171	61.71%
CYP3A4 substrate	+	0.6932	69.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6609	66.09%
CYP3A4 inhibition	-	0.6782	67.82%
CYP2C9 inhibition	-	0.6737	67.37%
CYP2C19 inhibition	-	0.8882	88.82%
CYP2D6 inhibition	+	0.5869	58.69%
CYP1A2 inhibition	+	0.5352	53.52%
CYP2C8 inhibition	+	0.4433	44.33%
CYP inhibitory promiscuity	-	0.6431	64.31%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9837	98.37%
Skin irritation	-	0.7622	76.22%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8750	87.50%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8654	86.54%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6064	60.64%
Acute Oral Toxicity (c)	III	0.6436	64.36%
Estrogen receptor binding	+	0.5445	54.45%
Androgen receptor binding	+	0.7493	74.93%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4815	48.15%
Aromatase binding	-	0.7775	77.75%
PPAR gamma	-	0.6253	62.53%
Honey bee toxicity	-	0.8219	82.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9462	94.62%

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	98.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.79%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.34%	94.45%
CHEMBL2535	P11166	Glucose transporter	92.12%	98.75%
CHEMBL2581	P07339	Cathepsin D	90.43%	98.95%
CHEMBL240	Q12809	HERG	90.15%	89.76%
CHEMBL5028	O14672	ADAM10	88.30%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.99%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	83.26%	98.59%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.06%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.00%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.73%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.13%	94.08%

Plants that contains it

• Alstonia sphaerocapitata
• Aspidosperma excelsum
• Catharanthus roseus
• Strychnos kasengaensis
• Strychnos matopensis
• Tabernaemontana africana
• Tabernaemontana corymbosa
• Tabernaemontana cymosa
• Tabernaemontana elegans
• Tabernaemontana pachysiphon

Cross-Links

• PubChem: 6504264
• LOTUS: LTS0114913
• wikiData: Q104253041