3-[(3S,5S,8S,9S,10R,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-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: 6c6b060e-ad97-42c7-b555-a07cee4b5e99
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8S,9S,10R,13R,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-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): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)CO)O)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)CO)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C41H64O19/c1-18-34(59-37-33(51)31(49)35(26(15-43)58-37)60-36-32(50)30(48)29(47)25(14-42)57-36)24(45)12-28(55-18)56-20-3-8-39(17-44)22-4-7-38(2)21(19-11-27(46)54-16-19)6-10-41(38,53)23(22)5-9-40(39,52)13-20/h11,18,20-26,28-37,42-45,47-53H,3-10,12-17H2,1-2H3/t18-,20+,21-,22+,23+,24+,25-,26-,28+,29-,30+,31-,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+/m1/s1
• InChI Key: FOSGZTYSSLMLOR-QKTZCIDGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₉
• Molecular Weight: 860.90 g/mol
• Exact Mass: 860.40417981 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -2.78
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 10

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	-	0.8930	89.30%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9083	90.83%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7926	79.26%
P-glycoprotein inhibitior	+	0.7193	71.93%
P-glycoprotein substrate	+	0.6665	66.65%
CYP3A4 substrate	+	0.7120	71.20%
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	-	0.5722	57.22%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9197	91.97%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8749	87.49%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7427	74.27%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9204	92.04%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.8528	85.28%
Androgen receptor binding	+	0.8093	80.93%
Thyroid receptor binding	-	0.6457	64.57%
Glucocorticoid receptor binding	+	0.6455	64.55%
Aromatase binding	+	0.7204	72.04%
PPAR gamma	+	0.7517	75.17%
Honey bee toxicity	-	0.6420	64.20%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.43%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.93%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.62%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.37%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.84%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	89.64%	95.93%
CHEMBL2581	P07339	Cathepsin D	87.82%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.30%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.12%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.18%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.95%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.61%	96.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.34%	96.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.86%	92.32%
CHEMBL5255	O00206	Toll-like receptor 4	81.81%	92.50%
CHEMBL4208	P20618	Proteasome component C5	81.77%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.51%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.68%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.37%	94.33%

Plants that contains it

• Erysimum marshallii

Cross-Links

• PubChem: 163076656
• LOTUS: LTS0161922
• wikiData: Q104998917