(1S,2S,3S,3'R,4R,4'R,6R)-3-ethyl-1,4'-dihydroxy-3'-methyl-11-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]spiro[5-oxa-10-azatricyclo[8.3.0.02,6]tridec-11-ene-4,5'-oxolane]-2',13-dione

Details

• Internal ID: 4e0ca1d5-79ed-47b9-bfe4-e0fb0ad9e961
• Taxonomy: Alkaloids and derivatives > Stemona alkaloids > Stemoamide-type alkaloids > Stichoneurine-type alkaloids
• IUPAC Name: (1S,2S,3S,3'R,4R,4'R,6R)-3-ethyl-1,4'-dihydroxy-3'-methyl-11-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]spiro[5-oxa-10-azatricyclo[8.3.0.02,6]tridec-11-ene-4,5'-oxolane]-2',13-dione
• SMILES (Canonical): CCC1C2C(CCCN3C2(C(=O)C=C3C4CC(C(=O)O4)C)O)OC15C(C(C(=O)O5)C)O
• SMILES (Isomeric): CC[C@H]1[C@H]2[C@@H](CCCN3[C@]2(C(=O)C=C3[C@@H]4C[C@@H](C(=O)O4)C)O)O[C@]15[C@@H]([C@H](C(=O)O5)C)O
• InChI: InChI=1S/C22H29NO8/c1-4-12-17-14(30-22(12)18(25)11(3)20(27)31-22)6-5-7-23-13(9-16(24)21(17,23)28)15-8-10(2)19(26)29-15/h9-12,14-15,17-18,25,28H,4-8H2,1-3H3/t10-,11+,12-,14+,15-,17-,18+,21+,22+/m0/s1
• InChI Key: SWPOVYVXDQCLSS-NOCJDDMUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₉NO₈
• Molecular Weight: 435.50 g/mol
• Exact Mass: 435.18931688 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.6104	61.04%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6742	67.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8710	87.10%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8787	87.87%
BSEP inhibitior	+	0.8021	80.21%
P-glycoprotein inhibitior	-	0.5450	54.50%
P-glycoprotein substrate	+	0.5890	58.90%
CYP3A4 substrate	+	0.6554	65.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8738	87.38%
CYP3A4 inhibition	-	0.8784	87.84%
CYP2C9 inhibition	-	0.8467	84.67%
CYP2C19 inhibition	-	0.8338	83.38%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8255	82.55%
CYP2C8 inhibition	-	0.6399	63.99%
CYP inhibitory promiscuity	-	0.9202	92.02%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4302	43.02%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7661	76.61%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.5624	56.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.6660	66.60%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.7575	75.75%
skin sensitisation	-	0.8560	85.60%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4669	46.69%
Acute Oral Toxicity (c)	III	0.5591	55.91%
Estrogen receptor binding	+	0.8058	80.58%
Androgen receptor binding	+	0.7783	77.83%
Thyroid receptor binding	+	0.5305	53.05%
Glucocorticoid receptor binding	+	0.6740	67.40%
Aromatase binding	+	0.5609	56.09%
PPAR gamma	+	0.5235	52.35%
Honey bee toxicity	-	0.7915	79.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.7092	70.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.25%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.60%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.34%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.76%	92.94%
CHEMBL2581	P07339	Cathepsin D	93.64%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.75%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	90.36%	89.63%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.11%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.89%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.76%	95.56%
CHEMBL4208	P20618	Proteasome component C5	88.24%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.63%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.68%	90.08%
CHEMBL226	P30542	Adenosine A1 receptor	85.20%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.59%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.26%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.28%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.12%	86.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.48%	94.66%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.61%	95.50%

Plants that contains it

• Stemona tuberosa

Cross-Links

• PubChem: 102575925
• LOTUS: LTS0162808
• wikiData: Q105262801