[(3S,5R,8R,9S,10S,13R,14S,16S,17S)-14-hydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxymethyl]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: 803534b8-0ecc-47d5-b3aa-dbb01b17eed6
• 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,17S)-14-hydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxymethyl]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)COCC8C(C(C(C(O8)O)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)COC[C@@H]8[C@H]([C@@H]([C@H]([C@@H](O8)O)O)O)O)O)O)O
• InChI: InChI=1S/C44H68O19/c1-19-39(63-41-38(52)36(50)34(48)29(62-41)18-56-17-28-33(47)35(49)37(51)40(53)61-28)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(46)57-16-21)27(59-20(2)45)15-44(25,43)54/h12,19,22-29,31-41,47-54H,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+/m1/s1
• InChI Key: SZLJFVCIFBITSD-QRNXZEPDSA-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: -1.90
• 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	+	0.8613	86.13%
Caco-2	-	0.8850	88.50%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8010	80.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9349	93.49%
P-glycoprotein inhibitior	+	0.7474	74.74%
P-glycoprotein substrate	+	0.7914	79.14%
CYP3A4 substrate	+	0.7481	74.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8963	89.63%
CYP3A4 inhibition	-	0.9115	91.15%
CYP2C9 inhibition	-	0.8993	89.93%
CYP2C19 inhibition	-	0.9186	91.86%
CYP2D6 inhibition	-	0.9477	94.77%
CYP1A2 inhibition	-	0.9364	93.64%
CYP2C8 inhibition	+	0.5970	59.70%
CYP inhibitory promiscuity	-	0.9702	97.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5349	53.49%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.5859	58.59%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6393	63.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7599	75.99%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.9012	90.12%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8966	89.66%
Acute Oral Toxicity (c)	I	0.8025	80.25%
Estrogen receptor binding	+	0.8505	85.05%
Androgen receptor binding	+	0.7824	78.24%
Thyroid receptor binding	-	0.5741	57.41%
Glucocorticoid receptor binding	+	0.7357	73.57%
Aromatase binding	+	0.6966	69.66%
PPAR gamma	+	0.8093	80.93%
Honey bee toxicity	-	0.5827	58.27%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9461	94.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.77%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.69%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.94%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.40%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.87%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.90%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.30%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.56%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.40%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.27%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	88.57%	92.50%
CHEMBL1871	P10275	Androgen Receptor	87.54%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.54%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.83%	97.33%
CHEMBL5028	O14672	ADAM10	84.70%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.90%	97.25%
CHEMBL4208	P20618	Proteasome component C5	83.63%	90.00%
CHEMBL2581	P07339	Cathepsin D	83.51%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.20%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.69%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.70%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.61%	99.23%

Plants that contains it

• Adenium obesum

Cross-Links

• PubChem: 162949605
• LOTUS: LTS0192800
• wikiData: Q105264226