(7E)-7-ethylidene-8-hydroxy-1'-methoxy-5-methylspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one

Details

• Internal ID: 8d970f15-65c8-4a30-aef8-843b85a4e0cb
• Taxonomy: Alkaloids and derivatives > Gelsemium alkaloids
• IUPAC Name: (7E)-7-ethylidene-8-hydroxy-1'-methoxy-5-methylspiro[11-oxa-5-azatricyclo[6.3.1.04,9]dodecane-2,3'-indole]-2'-one
• SMILES (Canonical): CC=C1CN(C2CC3(C4CC1(C2CO4)O)C5=CC=CC=C5N(C3=O)OC)C
• SMILES (Isomeric): C/C=C/1\CN(C2CC3(C4CC1(C2CO4)O)C5=CC=CC=C5N(C3=O)OC)C
• InChI: InChI=1S/C21H26N2O4/c1-4-13-11-22(2)17-9-20(18-10-21(13,25)15(17)12-27-18)14-7-5-6-8-16(14)23(26-3)19(20)24/h4-8,15,17-18,25H,9-12H2,1-3H3/b13-4+
• InChI Key: YZYOAMHMHRUBHH-YIXHJXPBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₄
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.18925731 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 5
• 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	+	0.9692	96.92%
Caco-2	+	0.7323	73.23%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.3718	37.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7956	79.56%
P-glycoprotein inhibitior	-	0.5135	51.35%
P-glycoprotein substrate	+	0.5957	59.57%
CYP3A4 substrate	+	0.6996	69.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3666	36.66%
CYP3A4 inhibition	-	0.6919	69.19%
CYP2C9 inhibition	-	0.7894	78.94%
CYP2C19 inhibition	-	0.7756	77.56%
CYP2D6 inhibition	-	0.8770	87.70%
CYP1A2 inhibition	-	0.8537	85.37%
CYP2C8 inhibition	-	0.7526	75.26%
CYP inhibitory promiscuity	-	0.9464	94.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.4844	48.44%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.9838	98.38%
Skin irritation	-	0.7614	76.14%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3764	37.64%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5011	50.11%
skin sensitisation	-	0.8338	83.38%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6170	61.70%
Acute Oral Toxicity (c)	III	0.5843	58.43%
Estrogen receptor binding	+	0.6611	66.11%
Androgen receptor binding	+	0.6276	62.76%
Thyroid receptor binding	+	0.6141	61.41%
Glucocorticoid receptor binding	+	0.5924	59.24%
Aromatase binding	-	0.5532	55.32%
PPAR gamma	-	0.7248	72.48%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9475	94.75%

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	96.01%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.72%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.25%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.25%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.40%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.50%	85.14%
CHEMBL4208	P20618	Proteasome component C5	84.40%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.92%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.82%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.96%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.18%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.71%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.74%	91.07%

Plants that contains it

• Gelsemium elegans

Cross-Links

• PubChem: 5318225
• NPASS: NPC97495