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

Details

• Internal ID: 65f65d0c-8026-4f68-a719-709db78949c5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5S,8R,9S,10R,13R,14S,16S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2(C3CCC4(CC(CCC4(C3CCC2(C1C5=CC(=O)OC5)C)C)OC6CC(C(C(O6)CO)OC7C(C(C(CO7)O)OC8C(C(CO8)(CO)O)O)O)O)O)O
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@@]2([C@@H]3CC[C@@]4(C[C@H](CC[C@@]4([C@H]3CC[C@@]2([C@H]1C5=CC(=O)OC5)C)C)O[C@H]6C[C@@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O[C@H]8[C@@H]([C@](CO8)(CO)O)O)O)O)O)O
• InChI: InChI=1S/C41H62O19/c1-19(44)56-26-13-41(52)23-6-9-40(51)12-21(4-7-37(40,2)22(23)5-8-38(41,3)30(26)20-10-28(47)53-15-20)57-29-11-24(45)32(27(14-42)58-29)59-35-31(48)33(25(46)16-54-35)60-36-34(49)39(50,17-43)18-55-36/h10,21-27,29-36,42-43,45-46,48-52H,4-9,11-18H2,1-3H3/t21-,22-,23+,24-,25+,26-,27+,29+,30-,31+,32-,33-,34-,35-,36-,37+,38+,39+,40-,41-/m0/s1
• InChI Key: QPJSGBVNFJZNCH-MLNKRKDESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₂O₁₉
• Molecular Weight: 858.90 g/mol
• Exact Mass: 858.38852974 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -1.96
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	0.8763	87.63%
OATP1B1 inhibitior	+	0.8661	86.61%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8958	89.58%
P-glycoprotein inhibitior	+	0.7358	73.58%
P-glycoprotein substrate	+	0.7825	78.25%
CYP3A4 substrate	+	0.7414	74.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8550	85.50%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.6984	69.84%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9114	91.14%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.8117	81.17%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5302	53.02%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7443	74.43%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8375	83.75%
Androgen receptor binding	+	0.7856	78.56%
Thyroid receptor binding	-	0.5934	59.34%
Glucocorticoid receptor binding	+	0.6640	66.40%
Aromatase binding	+	0.6483	64.83%
PPAR gamma	+	0.7558	75.58%
Honey bee toxicity	-	0.6248	62.48%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9628	96.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	97.92%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.82%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.73%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.04%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.33%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.08%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.29%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	91.97%	94.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.82%	97.25%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.00%	97.28%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.37%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.01%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.97%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.92%	82.69%
CHEMBL2581	P07339	Cathepsin D	87.69%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.30%	92.88%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.95%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.61%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.16%	96.77%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.03%	94.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.99%	91.07%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.55%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.65%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.45%	92.94%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.09%	81.11%
CHEMBL4208	P20618	Proteasome component C5	81.02%	90.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.95%	94.23%
CHEMBL5028	O14672	ADAM10	80.70%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.33%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.27%	96.38%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162848738
• LOTUS: LTS0151490
• wikiData: Q105225432