3-[(3S,5S,8R,9S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 4214a582-cb7d-4c3d-99da-97b3073d91fb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,11R,13R,14S,17R)-5,11,14-trihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(CC1(CCC3C2C(CC4(C3(CCC4C5=CC(=O)OC5)O)C)O)O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@@H](C[C@]1(CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O)O)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C29H44O11/c1-26-6-3-15(39-25-24(35)23(34)22(33)19(12-30)40-25)10-28(26,36)7-4-17-21(26)18(31)11-27(2)16(5-8-29(17,27)37)14-9-20(32)38-13-14/h9,15-19,21-25,30-31,33-37H,3-8,10-13H2,1-2H3/t15-,16+,17+,18+,19+,21+,22+,23-,24+,25-,26+,27+,28-,29-/m0/s1
• InChI Key: OIHKSETUJYIWTI-PLBBNNEUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₁
• Molecular Weight: 568.70 g/mol
• Exact Mass: 568.28836222 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.49
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8248	82.48%
Caco-2	-	0.8826	88.26%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	0.6221	62.21%
OATP1B1 inhibitior	+	0.9130	91.30%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6878	68.78%
P-glycoprotein inhibitior	-	0.5125	51.25%
P-glycoprotein substrate	-	0.6184	61.84%
CYP3A4 substrate	+	0.7047	70.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.9242	92.42%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4487	44.87%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9359	93.59%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8505	85.05%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7427	74.27%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7747	77.47%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.8298	82.98%
Androgen receptor binding	+	0.8285	82.85%
Thyroid receptor binding	-	0.6301	63.01%
Glucocorticoid receptor binding	+	0.5683	56.83%
Aromatase binding	+	0.7034	70.34%
PPAR gamma	+	0.5314	53.14%
Honey bee toxicity	-	0.7499	74.99%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9498	94.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.33%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.16%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.80%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.75%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.68%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.50%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.06%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.85%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.62%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.11%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	88.94%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.89%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.86%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.90%	93.04%
CHEMBL5255	O00206	Toll-like receptor 4	81.67%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.36%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.93%	92.94%
CHEMBL4208	P20618	Proteasome component C5	80.47%	90.00%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 163079494
• LOTUS: LTS0057555
• wikiData: Q105192508