3-[(3S,5R,8R,9S,10S,13R,14S,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-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: eaf68791-53f5-4275-a17e-999a58c24339
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,13R,14S,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-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)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(CC[C@H]5C6=CC(=O)OC6)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/C42H66O17/c1-19-37(59-39-36(49)34(47)32(45)28(58-39)18-53-17-27-31(44)33(46)35(48)38(50)57-27)26(52-4)15-30(55-19)56-22-7-10-40(2)21(14-22)5-6-25-24(40)8-11-41(3)23(9-12-42(25,41)51)20-13-29(43)54-16-20/h13,19,21-28,30-39,44-51H,5-12,14-18H2,1-4H3/t19-,21-,22+,23+,24+,25-,26+,27-,28-,30+,31-,32-,33+,34+,35-,36-,37-,38-,39+,40+,41-,42+/m1/s1
• InChI Key: PRLZDZHADKSLTR-HIZOUIHMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₇
• Molecular Weight: 843.00 g/mol
• Exact Mass: 842.43000063 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8784	87.84%
Caco-2	-	0.8924	89.24%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7748	77.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9060	90.60%
P-glycoprotein inhibitior	+	0.7434	74.34%
P-glycoprotein substrate	+	0.8026	80.26%
CYP3A4 substrate	+	0.7319	73.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.9445	94.45%
CYP2C9 inhibition	-	0.9048	90.48%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.9342	93.42%
CYP2C8 inhibition	-	0.5804	58.04%
CYP inhibitory promiscuity	-	0.9578	95.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5631	56.31%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.5890	58.90%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6824	68.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8433	84.33%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.9258	92.58%
Acute Oral Toxicity (c)	I	0.7402	74.02%
Estrogen receptor binding	+	0.8412	84.12%
Androgen receptor binding	+	0.8087	80.87%
Thyroid receptor binding	-	0.6476	64.76%
Glucocorticoid receptor binding	+	0.6647	66.47%
Aromatase binding	+	0.7287	72.87%
PPAR gamma	+	0.7726	77.26%
Honey bee toxicity	-	0.6067	60.67%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9245	92.45%

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	98.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.54%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.91%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.24%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.79%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.19%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.00%	96.77%
CHEMBL1871	P10275	Androgen Receptor	91.41%	96.43%
CHEMBL226	P30542	Adenosine A1 receptor	91.26%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.12%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.67%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.37%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.92%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.13%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.71%	95.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.42%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.02%	92.50%
CHEMBL2581	P07339	Cathepsin D	84.89%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.82%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.79%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.28%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.12%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.71%	97.14%
CHEMBL5028	O14672	ADAM10	80.01%	97.50%

Plants that contains it

• Adenium obesum

Cross-Links

• PubChem: 162908937
• LOTUS: LTS0195100
• wikiData: Q105213808