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

Details

• Internal ID: b4b06470-7870-4081-9f99-afb5e1adc5a9
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: (1S,2S,4S,6S,7R,8S)-6-ethyl-6-(hydroxymethyl)-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one
• SMILES (Canonical): CCC1(C2CC3C4(CC(C2CO3)N1)C5=CC=CC=C5N(C4=O)OC)CO
• SMILES (Isomeric): CC[C@]1([C@@H]2C[C@H]3[C@]4(C[C@@H]([C@H]2CO3)N1)C5=CC=CC=C5N(C4=O)OC)CO
• InChI: InChI=1S/C20H26N2O4/c1-3-19(11-23)14-8-17-20(9-15(21-19)12(14)10-26-17)13-6-4-5-7-16(13)22(25-2)18(20)24/h4-7,12,14-15,17,21,23H,3,8-11H2,1-2H3/t12-,14+,15-,17-,19+,20-/m0/s1
• InChI Key: ZREVWZNVVDYUMA-KXHDNATJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₄
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.18925731 g/mol
• Topological Polar Surface Area (TPSA): 71.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8957	89.57%
Caco-2	+	0.5490	54.90%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.4360	43.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8696	86.96%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6214	62.14%
P-glycoprotein inhibitior	-	0.7226	72.26%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6726	67.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3496	34.96%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.7556	75.56%
CYP2C19 inhibition	-	0.7604	76.04%
CYP2D6 inhibition	-	0.8309	83.09%
CYP1A2 inhibition	-	0.8294	82.94%
CYP2C8 inhibition	-	0.5702	57.02%
CYP inhibitory promiscuity	-	0.8810	88.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5783	57.83%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.9880	98.80%
Skin irritation	-	0.7714	77.14%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7939	79.39%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.5520	55.20%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6461	64.61%
Acute Oral Toxicity (c)	III	0.5836	58.36%
Estrogen receptor binding	+	0.7578	75.78%
Androgen receptor binding	+	0.6462	64.62%
Thyroid receptor binding	-	0.5173	51.73%
Glucocorticoid receptor binding	-	0.5422	54.22%
Aromatase binding	+	0.5606	56.06%
PPAR gamma	+	0.6484	64.84%
Honey bee toxicity	-	0.8154	81.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.7830	78.30%

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	98.53%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.47%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.04%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.48%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.73%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.30%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.24%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.30%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.71%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.72%	93.40%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 10948335
• NPASS: NPC151529