7-Ethylidene-1'-methoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one

Details

• Internal ID: 21365c26-70da-480e-a6ca-5165f9426e26
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: 7-ethylidene-1'-methoxyspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one
• SMILES (Canonical): CC=C1CNC2CC3(C4CC1C2CO4)C5=CC=CC=C5N(C3=O)OC
• SMILES (Isomeric): CC=C1CNC2CC3(C4CC1C2CO4)C5=CC=CC=C5N(C3=O)OC
• InChI: InChI=1S/C20H24N2O3/c1-3-12-10-21-16-9-20(18-8-13(12)14(16)11-25-18)15-6-4-5-7-17(15)22(24-2)19(20)23/h3-7,13-14,16,18,21H,8-11H2,1-2H3
• InChI Key: ZXRGGMATGWCUBP-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₃
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.17869263 g/mol
• Topological Polar Surface Area (TPSA): 50.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9899	98.99%
Caco-2	+	0.6866	68.66%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.4219	42.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8743	87.43%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7735	77.35%
P-glycoprotein inhibitior	-	0.5256	52.56%
P-glycoprotein substrate	-	0.5534	55.34%
CYP3A4 substrate	+	0.6791	67.91%
CYP2C9 substrate	-	0.8056	80.56%
CYP2D6 substrate	+	0.3519	35.19%
CYP3A4 inhibition	-	0.8213	82.13%
CYP2C9 inhibition	-	0.7178	71.78%
CYP2C19 inhibition	-	0.6838	68.38%
CYP2D6 inhibition	-	0.8563	85.63%
CYP1A2 inhibition	-	0.6791	67.91%
CYP2C8 inhibition	+	0.4462	44.62%
CYP inhibitory promiscuity	-	0.7368	73.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5141	51.41%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9917	99.17%
Skin irritation	-	0.7626	76.26%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7634	76.34%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8286	82.86%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4828	48.28%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	+	0.5555	55.55%
Androgen receptor binding	+	0.6348	63.48%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.6140	61.40%
Aromatase binding	-	0.5844	58.44%
PPAR gamma	-	0.5857	58.57%
Honey bee toxicity	-	0.7126	71.26%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9020	90.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.64%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.53%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.66%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.53%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.87%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.03%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.61%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	81.33%	94.75%

Plants that contains it

• Gelsemium rankinii

Cross-Links

• PubChem: 129606
• LOTUS: LTS0186255
• wikiData: Q105385734