9-Ethylidene-2-(hydroxymethyl)-1'-methylspiro[7-azatricyclo[4.3.1.03,7]decane-5,3'-indole]-2'-one

Details

• Internal ID: ff52e209-473f-4b8d-be08-b71319a0b8b4
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: 9-ethylidene-2-(hydroxymethyl)-1'-methylspiro[7-azatricyclo[4.3.1.03,7]decane-5,3'-indole]-2'-one
• SMILES (Canonical): CC=C1CN2C3CC1C(C2CC34C5=CC=CC=C5N(C4=O)C)CO
• SMILES (Isomeric): CC=C1CN2C3CC1C(C2CC34C5=CC=CC=C5N(C4=O)C)CO
• InChI: InChI=1S/C20H24N2O2/c1-3-12-10-22-17-9-20(18(22)8-13(12)14(17)11-23)15-6-4-5-7-16(15)21(2)19(20)24/h3-7,13-14,17-18,23H,8-11H2,1-2H3
• InChI Key: RCIQQZVEOPKKID-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 43.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 3
• 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	+	0.9454	94.54%
Caco-2	+	0.8303	83.03%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6815	68.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8699	86.99%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6985	69.85%
P-glycoprotein inhibitior	-	0.7102	71.02%
P-glycoprotein substrate	+	0.5100	51.00%
CYP3A4 substrate	+	0.6108	61.08%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	+	0.3972	39.72%
CYP3A4 inhibition	-	0.7219	72.19%
CYP2C9 inhibition	-	0.6756	67.56%
CYP2C19 inhibition	-	0.7205	72.05%
CYP2D6 inhibition	-	0.7267	72.67%
CYP1A2 inhibition	-	0.6528	65.28%
CYP2C8 inhibition	-	0.7610	76.10%
CYP inhibitory promiscuity	-	0.7008	70.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6524	65.24%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9911	99.11%
Skin irritation	-	0.7779	77.79%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7197	71.97%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.8354	83.54%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6044	60.44%
Acute Oral Toxicity (c)	III	0.5104	51.04%
Estrogen receptor binding	+	0.6604	66.04%
Androgen receptor binding	+	0.6785	67.85%
Thyroid receptor binding	-	0.4948	49.48%
Glucocorticoid receptor binding	-	0.6172	61.72%
Aromatase binding	-	0.5918	59.18%
PPAR gamma	-	0.5671	56.71%
Honey bee toxicity	-	0.9183	91.83%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9439	94.39%

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	97.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.14%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.20%	95.83%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.38%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.56%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.86%	82.69%
CHEMBL4208	P20618	Proteasome component C5	83.10%	90.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.23%	93.00%

Plants that contains it

• Alstonia angustifolia

Cross-Links

• PubChem: 74033534
• LOTUS: LTS0052784
• wikiData: Q105233695