(1R,2S,4S,6R,7R,8S)-6-ethyl-6-(hydroxymethyl)-1'-methoxy-5-methylspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one

Details

• Internal ID: 241ac741-58a4-4715-a666-bee65ab6e254
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: (1R,2S,4S,6R,7R,8S)-6-ethyl-6-(hydroxymethyl)-1'-methoxy-5-methylspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one
• InChI: InChI=1S/C21H28N2O4/c1-4-20(12-24)15-9-18-21(10-17(22(20)2)13(15)11-27-18)14-7-5-6-8-16(14)23(26-3)19(21)25/h5-8,13,15,17-18,24H,4,9-12H2,1-3H3/t13-,15+,17-,18+,20-,21-/m0/s1
• InChI Key: OSYOERKDINCIMG-IKMCGIAPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈N₂O₄
• Molecular Weight: 372.50 g/mol
• Exact Mass: 372.20490738 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9159	91.59%
Caco-2	+	0.7634	76.34%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3876	38.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8752	87.52%
P-glycoprotein inhibitior	-	0.5394	53.94%
P-glycoprotein substrate	+	0.5404	54.04%
CYP3A4 substrate	+	0.6688	66.88%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	+	0.3995	39.95%
CYP3A4 inhibition	-	0.6315	63.15%
CYP2C9 inhibition	-	0.6658	66.58%
CYP2C19 inhibition	-	0.6883	68.83%
CYP2D6 inhibition	-	0.8263	82.63%
CYP1A2 inhibition	-	0.8755	87.55%
CYP2C8 inhibition	-	0.6067	60.67%
CYP inhibitory promiscuity	-	0.8200	82.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5708	57.08%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.9900	99.00%
Skin irritation	-	0.7814	78.14%
Skin corrosion	-	0.9320	93.20%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7841	78.41%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5645	56.45%
skin sensitisation	-	0.8500	85.00%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8111	81.11%
Acute Oral Toxicity (c)	III	0.5845	58.45%
Estrogen receptor binding	+	0.8007	80.07%
Androgen receptor binding	+	0.6586	65.86%
Thyroid receptor binding	+	0.5585	55.85%
Glucocorticoid receptor binding	+	0.5720	57.20%
Aromatase binding	+	0.5522	55.22%
PPAR gamma	-	0.5266	52.66%
Honey bee toxicity	-	0.8149	81.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7998	79.98%

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	98.49%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.96%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.76%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.12%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.83%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.79%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.51%	97.14%
CHEMBL4208	P20618	Proteasome component C5	83.92%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.96%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.79%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.78%	85.14%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 102061673
• LOTUS: LTS0018243
• wikiData: Q105199395