[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

Details

• Internal ID: 9a881849-c371-488a-9f9b-9254e2948044
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)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](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C44H68O19/c1-19-39(63-41-38(53)36(51)34(49)29(62-41)18-57-40-37(52)35(50)33(48)28(16-45)61-40)26(55-5)14-31(58-19)60-23-8-10-42(3)22(13-23)6-7-25-24(42)9-11-43(4)32(21-12-30(47)56-17-21)27(59-20(2)46)15-44(25,43)54/h12,19,22-29,31-41,45,48-54H,6-11,13-18H2,1-5H3/t19-,22+,23-,24-,25+,26-,27-,28+,29+,31-,32-,33+,34+,35-,36-,37+,38+,39-,40+,41-,42-,43+,44-/m0/s1
• InChI Key: PKZLCDIEFSFXDK-GQGLVPEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₈O₁₉
• Molecular Weight: 901.00 g/mol
• Exact Mass: 900.43547994 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.67
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8882	88.82%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9351	93.51%
P-glycoprotein inhibitior	+	0.7478	74.78%
P-glycoprotein substrate	+	0.7783	77.83%
CYP3A4 substrate	+	0.7440	74.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.5906	59.06%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6093	60.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7858	78.58%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6592	65.92%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7633	76.33%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8592	85.92%
Androgen receptor binding	+	0.7840	78.40%
Thyroid receptor binding	-	0.5876	58.76%
Glucocorticoid receptor binding	+	0.7253	72.53%
Aromatase binding	+	0.6928	69.28%
PPAR gamma	+	0.8039	80.39%
Honey bee toxicity	-	0.5910	59.10%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	98.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.79%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.55%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.83%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.12%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.95%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	89.74%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.11%	94.33%
CHEMBL1871	P10275	Androgen Receptor	86.94%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.46%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.96%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.91%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.62%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.41%	92.94%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.20%	81.11%
CHEMBL2581	P07339	Cathepsin D	84.07%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.32%	89.00%
CHEMBL5028	O14672	ADAM10	83.00%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.68%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.57%	90.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.85%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.61%	99.23%

Plants that contains it

• Nerium oleander

Cross-Links

• PubChem: 162926809
• LOTUS: LTS0117410
• wikiData: Q105210772